CH615675A5 - - Google Patents
Download PDFInfo
- Publication number
- CH615675A5 CH615675A5 CH180574A CH180574A CH615675A5 CH 615675 A5 CH615675 A5 CH 615675A5 CH 180574 A CH180574 A CH 180574A CH 180574 A CH180574 A CH 180574A CH 615675 A5 CH615675 A5 CH 615675A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- acid
- compound
- hydrogen
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 117
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 114
- -1 phenacyl group Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 48
- 239000011541 reaction mixture Substances 0.000 claims description 44
- 235000011054 acetic acid Nutrition 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 31
- 150000001539 azetidines Chemical class 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 241001104043 Syringa Species 0.000 claims description 12
- 235000004338 Syringa vulgaris Nutrition 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- RHLBOBPOIZROJX-UHFFFAOYSA-N 1-acetylpyrrolidine-2,5-dione Chemical compound CC(=O)N1C(=O)CCC1=O RHLBOBPOIZROJX-UHFFFAOYSA-N 0.000 claims description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 6
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- INZUQGFQRYAKQQ-UHFFFAOYSA-N 2-acetylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(=O)C)C(=O)C2=C1 INZUQGFQRYAKQQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 4
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 4
- FVVXWRGARUACNW-UHFFFAOYSA-N 3-methylisoquinoline Chemical compound C1=CC=C2C=NC(C)=CC2=C1 FVVXWRGARUACNW-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000002210 silicon-based material Substances 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 claims description 3
- ZMZMWZJOEIWLQL-UHFFFAOYSA-N 1-[bis(ethylsulfonyl)methylsulfonyl]ethane Chemical compound CCS(=O)(=O)C(S(=O)(=O)CC)S(=O)(=O)CC ZMZMWZJOEIWLQL-UHFFFAOYSA-N 0.000 claims description 2
- FFTLEZMCZZAUQJ-UHFFFAOYSA-N 2,2-dinitroacetonitrile Chemical compound [O-][N+](=O)C(C#N)[N+]([O-])=O FFTLEZMCZZAUQJ-UHFFFAOYSA-N 0.000 claims description 2
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 claims description 2
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001243 acetic acids Chemical class 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims description 2
- 229940005991 chloric acid Drugs 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- SMRRYUGQTFYZGD-UHFFFAOYSA-K diacetyloxythallanyl acetate Chemical compound [Tl+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SMRRYUGQTFYZGD-UHFFFAOYSA-K 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- AHSBSUVHXDIAEY-UHFFFAOYSA-K manganese(iii) acetate Chemical compound [Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AHSBSUVHXDIAEY-UHFFFAOYSA-K 0.000 claims description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- JHRFTUUPRRIVKE-UHFFFAOYSA-N prop-1-ene-1,1,2,3,3-pentacarbonitrile Chemical compound N#CC(C#N)C(C#N)=C(C#N)C#N JHRFTUUPRRIVKE-UHFFFAOYSA-N 0.000 claims description 2
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical class OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 claims 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- ZBNYCYQDFZWFFU-UHFFFAOYSA-N 1h-imidazole;1-methylimidazole Chemical compound C1=CNC=N1.CN1C=CN=C1 ZBNYCYQDFZWFFU-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 claims 1
- 229910018540 Si C Inorganic materials 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 229960004011 methenamine Drugs 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 34
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 229940113088 dimethylacetamide Drugs 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 229930182555 Penicillin Natural products 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000003377 silicon compounds Chemical class 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 229940049954 penicillin Drugs 0.000 description 12
- YUWVMABNHZEMGO-UHFFFAOYSA-N 1-trimethylsilylpyrrolidine-2,5-dione Chemical compound C[Si](C)(C)N1C(=O)CCC1=O YUWVMABNHZEMGO-UHFFFAOYSA-N 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- ZRAPHEBMDYQXKR-UHFFFAOYSA-N 2-trimethylsilylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N([Si](C)(C)C)C(=O)C2=C1 ZRAPHEBMDYQXKR-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- 229930186147 Cephalosporin Natural products 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
- 229940124587 cephalosporin Drugs 0.000 description 6
- 150000001780 cephalosporins Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- FTWWABXHBBWBNV-UHFFFAOYSA-N 4,4-dimethyl-1-trimethylsilylpiperidine-2,6-dione Chemical compound CC1(C)CC(=O)N([Si](C)(C)C)C(=O)C1 FTWWABXHBBWBNV-UHFFFAOYSA-N 0.000 description 3
- HTUBIXOOXNBTCK-UHFFFAOYSA-N 4-ethyl-4-methyl-1-trimethylsilylpiperidine-2,6-dione Chemical compound CCC1(C)CC(=O)N([Si](C)(C)C)C(=O)C1 HTUBIXOOXNBTCK-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- MLSIOVIWWMNVQR-UHFFFAOYSA-N 2-[2-(2,5-dioxopyrrolidin-1-yl)sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound C=1C=CC=CC=1CC(=O)NC1C(=O)N(C(C(=C)C)C(O)=O)C1SN1C(=O)CCC1=O MLSIOVIWWMNVQR-UHFFFAOYSA-N 0.000 description 2
- GCBXXRPFVSAYKI-UHFFFAOYSA-N 2-trimethylsilyl-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)N([Si](C)(C)C)C(=O)C21 GCBXXRPFVSAYKI-UHFFFAOYSA-N 0.000 description 2
- WLDMPODMCFGWAA-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical class C1CCCC2C(=O)NC(=O)C21 WLDMPODMCFGWAA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- DNPOVSLJNLLGMA-NCQUQDSPSA-N (2S,4R,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C([S@]2=O)(C)C)C(O)=O)C(=O)COC1=CC=CC=C1 DNPOVSLJNLLGMA-NCQUQDSPSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SFZQZAQRMKDJHP-UHFFFAOYSA-N 1,5,5-trimethyl-3-trimethylsilylimidazolidine-2,4-dione Chemical compound CN1C(=O)N([Si](C)(C)C)C(=O)C1(C)C SFZQZAQRMKDJHP-UHFFFAOYSA-N 0.000 description 1
- ZNYIPTYJBRGSSL-UHFFFAOYSA-N 1,5,5-trimethylimidazolidine-2,4-dione Chemical compound CN1C(=O)NC(=O)C1(C)C ZNYIPTYJBRGSSL-UHFFFAOYSA-N 0.000 description 1
- HYBDSXBLGCQKRE-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)ethanone Chemical compound CC(=O)C1=C(Cl)C=CC=C1Cl HYBDSXBLGCQKRE-UHFFFAOYSA-N 0.000 description 1
- QMSVNDSDEZTYAS-UHFFFAOYSA-N 1-bromo-1-chloroethane Chemical compound CC(Cl)Br QMSVNDSDEZTYAS-UHFFFAOYSA-N 0.000 description 1
- KIAMPLQEZAMORJ-UHFFFAOYSA-N 1-ethoxy-2-[2-(2-ethoxyethoxy)ethoxy]ethane Chemical compound CCOCCOCCOCCOCC KIAMPLQEZAMORJ-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KQWRILJSSKKQJM-UHFFFAOYSA-N 1-prop-2-enylazetidine Chemical class C=CCN1CCC1 KQWRILJSSKKQJM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LDCPWYYVCHVWBP-UHFFFAOYSA-N 3-trimethylsilylpyrrolidine-2,5-dione Chemical compound C[Si](C)(C)C1CC(=O)NC1=O LDCPWYYVCHVWBP-UHFFFAOYSA-N 0.000 description 1
- YUJCWMGBRDBPDL-UHFFFAOYSA-N 4,4-dimethylpiperidine-2,6-dione Chemical compound CC1(C)CC(=O)NC(=O)C1 YUJCWMGBRDBPDL-UHFFFAOYSA-N 0.000 description 1
- ORRZGUBHBVWWOP-UHFFFAOYSA-N 4-ethyl-4-methylpiperidine-2,6-dione Chemical compound CCC1(C)CC(=O)NC(=O)C1 ORRZGUBHBVWWOP-UHFFFAOYSA-N 0.000 description 1
- NESKCZJINZUBPH-UHFFFAOYSA-N 4-trimethylsilylisoindole-1,3-dione Chemical compound C[Si](C)(C)C1=CC=CC2=C1C(=O)NC2=O NESKCZJINZUBPH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 101150046236 CNR1 gene Proteins 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical group [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- KSEMETYAQIUBQB-UHFFFAOYSA-N n,n-diethylmethanesulfonamide Chemical compound CCN(CC)S(C)(=O)=O KSEMETYAQIUBQB-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 235000021178 picnic Nutrition 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JFHIHGKRIMGLJR-UHFFFAOYSA-N trimethylsilyl 2-[2-(1,3-dioxoisoindol-2-yl)sulfanyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound O=C1N(C(C(=C)C)C(=O)O[Si](C)(C)C)C(SN2C(C3=CC=CC=C3C2=O)=O)C1NC(=O)COC1=CC=CC=C1 JFHIHGKRIMGLJR-UHFFFAOYSA-N 0.000 description 1
- MNLGNPBGHGCSHF-UHFFFAOYSA-N trimethylsilyl 2-[2-(1,3-dioxoisoindol-2-yl)sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C[Si](OC(=O)C(C(=C)C)N1C(C(C1SN1C(C=2C(C1=O)=CC=CC=2)=O)NC(CC1=CC=CC=C1)=O)=O)(C)C MNLGNPBGHGCSHF-UHFFFAOYSA-N 0.000 description 1
- QYVZUAZPUVORRG-UHFFFAOYSA-N trimethylsilyl 2-[2-(2,5-dioxopyrrolidin-1-yl)sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1CC(=O)NC1C(=O)N(C(C(=C)C)C(=O)O[Si](C)(C)C)C1SN1C(=O)CCC1=O QYVZUAZPUVORRG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 150000003952 β-lactams Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/08—Preparation by forming the ring or condensed ring systems
- C07D501/10—Preparation by forming the ring or condensed ring systems from compounds containing the penicillin ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB657673A GB1465893A (en) | 1973-02-09 | 1973-02-09 | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
Publications (1)
Publication Number | Publication Date |
---|---|
CH615675A5 true CH615675A5 (sv) | 1980-02-15 |
Family
ID=9817015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH180574A CH615675A5 (sv) | 1973-02-09 | 1974-02-08 |
Country Status (30)
Country | Link |
---|---|
US (2) | US3966738A (sv) |
JP (1) | JPS5734836B2 (sv) |
AR (1) | AR204821A1 (sv) |
AT (1) | AT331399B (sv) |
AU (1) | AU6540874A (sv) |
BE (1) | BE810808A (sv) |
BR (1) | BR7400904D0 (sv) |
CA (1) | CA1042873A (sv) |
CH (1) | CH615675A5 (sv) |
CS (1) | CS189623B2 (sv) |
DD (1) | DD111580A5 (sv) |
DE (1) | DE2406165A1 (sv) |
DK (1) | DK153949C (sv) |
ES (1) | ES423051A1 (sv) |
FI (1) | FI63583C (sv) |
FR (1) | FR2260583B1 (sv) |
GB (1) | GB1465893A (sv) |
HU (1) | HU167925B (sv) |
IE (1) | IE38833B1 (sv) |
IL (1) | IL44176A (sv) |
IN (1) | IN139732B (sv) |
IT (1) | IT1055549B (sv) |
LU (1) | LU69361A1 (sv) |
NL (1) | NL181991C (sv) |
NO (1) | NO142815C (sv) |
PH (1) | PH9901A (sv) |
RO (1) | RO67307A (sv) |
SE (1) | SE417958B (sv) |
YU (1) | YU36723B (sv) |
ZA (1) | ZA74831B (sv) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
US4046761A (en) * | 1974-02-08 | 1977-09-06 | Gist-Brocades N.V. | Process for preparing cephalosporin derivatives |
US4159266A (en) * | 1974-12-24 | 1979-06-26 | Eli Lilly And Company | Method of preparation of 3-methylenecephams |
US4018761A (en) * | 1975-02-19 | 1977-04-19 | E. R. Squibb & Sons, Inc. | Thio-β-lactam cephalosporins |
GB1472864A (en) * | 1975-04-05 | 1977-05-11 | Farmaceutici Italia | Method of preparing cephalosporins |
IT1063088B (it) * | 1976-06-01 | 1985-02-11 | Dobfar Spa | Derivati azetidinonici e procedimento per la preparazione di cefalosporine |
US4322347A (en) * | 1978-04-03 | 1982-03-30 | Bristol-Myers Company | 2-Carbamoyloxymethyl-penicillin derivatives |
GB2045236A (en) * | 1979-03-26 | 1980-10-29 | Hoechst Uk Ltd | Oxapenem derivatives |
GB2099817B (en) * | 1981-04-10 | 1985-05-15 | Otsuka Kagaku Yakuhin | Azetidinone derivatives and process for the preparation of the same |
US6383773B2 (en) | 1998-04-23 | 2002-05-07 | Massachusetts Institute Of Technology | Penicillin conversion |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK136480B (da) * | 1969-03-11 | 1977-10-17 | Glaxo Lab Ltd | Fremgangsmåde til fremstilling af 7beta-acylamido-3-metylceph-3-em-4-karboxylsyreestere ved omlejring af en 6beta-acylamidopenicillansyre-1-oxydester. |
US3853861A (en) * | 1969-03-18 | 1974-12-10 | Lilly Co Eli | Cephalexin intermediate |
GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
US3843637A (en) * | 1971-05-11 | 1974-10-22 | Bristol Myers Co | Process for rearranging 6-acylamidopenicillanic acid-1-oxides to 7-acyla mido-3-methyl-ceph-3-em-4-carboxylic acids |
US3840556A (en) * | 1971-05-28 | 1974-10-08 | Lilly Co Eli | Penicillin conversion by halogen electrophiles and anti-bacterials derived thereby |
US3720666A (en) * | 1971-09-02 | 1973-03-13 | American Home Prod | 6-(substituted-4-oxouretidino-1-yl)penicillanic acids |
US3736318A (en) * | 1971-09-09 | 1973-05-29 | American Home Prod | 6-(2-substituted-3-phenyl-2h-isoindole-1-carboxamido)penicillanic acids |
US3944545A (en) * | 1972-05-10 | 1976-03-16 | Eli Lilly And Company | Process for preparing desacetoxycephalosporins |
GB1431174A (en) * | 1972-06-30 | 1976-04-07 | Clin Midy | Process for the conversion of a penicillin s-oxide into a corresponding desacetoxycephalosporin |
JPS4988892A (sv) * | 1972-12-28 | 1974-08-24 | ||
US3962277A (en) * | 1973-02-09 | 1976-06-08 | Gist-Brocades N.V. | Acetidine derivatives |
GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
US4008221A (en) * | 1973-11-07 | 1977-02-15 | Richardson-Merrell Inc. | 6-[(2,4-Dioxo-1-pyrimidinyl)acylamino]penicillin derivatives |
GB1483526A (en) * | 1974-02-08 | 1977-08-24 | Gist Brocades Nv | Azetidine derivatives |
CH602746A5 (sv) * | 1974-03-12 | 1978-07-31 | Hoffmann La Roche | |
DE2440268A1 (de) * | 1974-08-22 | 1976-03-04 | Bayer Ag | Beta-lactamantibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
US4009160A (en) * | 1974-11-12 | 1977-02-22 | Pfizer Inc. | Aminomethylarylmethylpenicillin derivatives |
DE2457464A1 (de) * | 1974-12-05 | 1976-06-10 | Hoechst Ag | Acylaminopenicillansaeuren und verfahren zu ihrer herstellung |
US3953440A (en) * | 1974-12-13 | 1976-04-27 | Eli Lilly And Company | Deacetoxycephalosporins via penicillin sulfoxide rearrangement |
JPS5195090A (en) * | 1975-02-14 | 1976-08-20 | 66 * dd22 * 33 hidorokishipiridajin 44 karubokishiamido * 22 * paraahidorokishifueniru * asetoamido * penishiransanno seiho |
-
1973
- 1973-02-09 GB GB657673A patent/GB1465893A/en not_active Expired
-
1974
- 1974-01-01 AR AR252251A patent/AR204821A1/es active
- 1974-02-08 US US05/440,725 patent/US3966738A/en not_active Expired - Lifetime
- 1974-02-08 ES ES423051A patent/ES423051A1/es not_active Expired
- 1974-02-08 FR FR7404359A patent/FR2260583B1/fr not_active Expired
- 1974-02-08 CH CH180574A patent/CH615675A5/de not_active IP Right Cessation
- 1974-02-08 HU HUGI199A patent/HU167925B/hu unknown
- 1974-02-08 BE BE140725A patent/BE810808A/xx not_active IP Right Cessation
- 1974-02-08 BR BR74904A patent/BR7400904D0/pt unknown
- 1974-02-08 FI FI364/74A patent/FI63583C/fi active
- 1974-02-08 YU YU0336/74A patent/YU36723B/xx unknown
- 1974-02-08 RO RO7477586A patent/RO67307A/ro unknown
- 1974-02-08 JP JP1612274A patent/JPS5734836B2/ja not_active Expired
- 1974-02-08 LU LU69361A patent/LU69361A1/xx unknown
- 1974-02-08 IT IT67350/74A patent/IT1055549B/it active
- 1974-02-08 DE DE19742406165 patent/DE2406165A1/de not_active Withdrawn
- 1974-02-08 SE SE7401707A patent/SE417958B/sv not_active IP Right Cessation
- 1974-02-08 AU AU65408/74A patent/AU6540874A/en not_active Expired
- 1974-02-08 ZA ZA740831A patent/ZA74831B/xx unknown
- 1974-02-08 DK DK069174A patent/DK153949C/da not_active IP Right Cessation
- 1974-02-08 CS CS74918A patent/CS189623B2/cs unknown
- 1974-02-08 DD DD176471A patent/DD111580A5/xx unknown
- 1974-02-08 IE IE243/74A patent/IE38833B1/xx unknown
- 1974-02-08 CA CA192,253A patent/CA1042873A/en not_active Expired
- 1974-02-08 AT AT100774A patent/AT331399B/de not_active IP Right Cessation
- 1974-02-08 IL IL44176A patent/IL44176A/en unknown
- 1974-02-08 PH PH15491*A patent/PH9901A/en unknown
- 1974-02-08 NL NLAANVRAGE7401730,A patent/NL181991C/xx not_active IP Right Cessation
- 1974-02-08 NO NO740431A patent/NO142815C/no unknown
- 1974-02-08 IN IN264/CAL/74A patent/IN139732B/en unknown
-
1975
- 1975-10-21 US US05/624,332 patent/US4282145A/en not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69428280T2 (de) | Verfahren zur herstellung von azetidinonen | |
CH634579A5 (en) | Process for preparing cephem compounds | |
DE69231874T2 (de) | Verfahren zur herstellung von 4-substituierten azetidinon-derivaten | |
DE3788463T2 (de) | 3-Beta-(3,4-disubstituiertes succinimido)azetidinone. | |
CH615675A5 (sv) | ||
DE2258221A1 (de) | Verfahren zum herstellen neuartiger antibiotischer verbindungen | |
EP0111934B1 (de) | Cephalosporinderivate und Verfahren zu ihrer Herstellung | |
DE2240224B2 (de) | Verfahren zur Herstellung von A3 ^methyl-cephem- 4-carbonsäuren | |
DD226894A5 (de) | Neues verfahren zur herstellung von cephalosporinen | |
CH645384A5 (de) | 3-phosphonocephalosporansaeure-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel. | |
EP0137442A2 (de) | Cephalosporinderivate und Verfahren zu ihrer Herstellung | |
DE2265641C2 (de) | 7-Iminocephalosporine | |
DE2462383A1 (de) | Verfahren zur herstellung von antibiotischen mitteln | |
CH636618A5 (en) | 1-Oxadethiacepham compounds, and a process for preparing them | |
US4010156A (en) | Process for the rearrangement of penicillins to cephalosporins and intermediate compounds thereof | |
DE2107650C3 (sv) | ||
DE2505280A1 (de) | Azetidinderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von cephalosporansaeurederivaten | |
US3932398A (en) | 3-Halo-cepham derivatives | |
AT328085B (de) | Verfahren zur herstellung neuer penicilline | |
DE2333256A1 (de) | Halogenpenam- und halogencephamderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
DE2215039A1 (de) | Neue Acyloxyalkylesterderivate von Penicillin und Cephalosporin | |
DE2429166A1 (de) | Verfahren zur selektiven spaltung der amidsaeurefunktion eines 7-(amidsaeure)cephalosporins | |
DE3854215T2 (de) | Alkenylsilylazetidinon-Zwischenprodukte für Carbapeneme. | |
DE2911787C2 (de) | Carbacephemderivate und ihre Verwendung | |
US3962277A (en) | Acetidine derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |