CS197217B2 - Method of conversion of penicilin sulphoxide into deacetoxy cephalosporin and lithium salt of the same - Google Patents
Method of conversion of penicilin sulphoxide into deacetoxy cephalosporin and lithium salt of the same Download PDFInfo
- Publication number
- CS197217B2 CS197217B2 CS733319A CS331973A CS197217B2 CS 197217 B2 CS197217 B2 CS 197217B2 CS 733319 A CS733319 A CS 733319A CS 331973 A CS331973 A CS 331973A CS 197217 B2 CS197217 B2 CS 197217B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- phenyl
- acid
- group
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 43
- 238000006243 chemical reaction Methods 0.000 title claims description 24
- 229910003002 lithium salt Inorganic materials 0.000 title claims description 11
- 159000000002 lithium salts Chemical class 0.000 title claims description 9
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 title abstract 2
- NNQIJOYQWYKBOW-UHFFFAOYSA-N desacetoxycephalosphorin G Natural products S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 NNQIJOYQWYKBOW-UHFFFAOYSA-N 0.000 title 1
- -1 2-iodoethyl Chemical group 0.000 claims abstract description 103
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000006502 nitrobenzyl group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 239000011737 fluorine Substances 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 79
- 239000002253 acid Substances 0.000 claims description 39
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 38
- 239000011541 reaction mixture Substances 0.000 claims description 34
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 32
- 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 claims description 25
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 19
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 19
- 150000003462 sulfoxides Chemical class 0.000 claims description 17
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229930186147 Cephalosporin Natural products 0.000 claims description 9
- 229940124587 cephalosporin Drugs 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002642 lithium compounds Chemical class 0.000 claims description 5
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000005543 phthalimide group Chemical group 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- BRADTAJXVOECJE-UHFFFAOYSA-N 2-hydroxysulfanylazetidine Chemical class OSC1CCN1 BRADTAJXVOECJE-UHFFFAOYSA-N 0.000 abstract description 20
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract description 14
- 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 abstract description 12
- 229930182555 Penicillin Natural products 0.000 abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 8
- 229940049954 penicillin Drugs 0.000 abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 7
- 150000007513 acids Chemical class 0.000 abstract description 5
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract description 3
- 125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 abstract description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005544 phthalimido group Chemical group 0.000 abstract description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000005179 haloacetyl group Chemical group 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000000543 intermediate Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 11
- 238000006798 ring closing metathesis reaction Methods 0.000 description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001780 cephalosporins Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000006884 silylation reaction Methods 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- YSJGVKHCAVGBIT-AVKWCDSFSA-N (4-nitrophenyl)methyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 YSJGVKHCAVGBIT-AVKWCDSFSA-N 0.000 description 3
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930195708 Penicillin V Natural products 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 229940056367 penicillin v Drugs 0.000 description 3
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IWAAXRFPRHQKAZ-RKOYOZNISA-N (6R)-3-methyl-4-[(4-nitrophenyl)methyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound [N+](=O)([O-])C1=CC=C(CC2S[C@H]3N(C(=C2C)C(=O)O)C(C3NC(COC3=CC=CC=C3)=O)=O)C=C1 IWAAXRFPRHQKAZ-RKOYOZNISA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PBRCJCQXPAJPEL-PVQCJRHBSA-N methyl (6r)-7-(1,3-dioxoisoindol-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1[C@H]2SCC(C)=C(C(=O)OC)N2C1=O PBRCJCQXPAJPEL-PVQCJRHBSA-N 0.000 description 2
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 2
- 235000007708 morin Nutrition 0.000 description 2
- UHVFJVDNBBBJAV-UHFFFAOYSA-N n-triphenylsilylacetamide Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(NC(=O)C)C1=CC=CC=C1 UHVFJVDNBBBJAV-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003860 tertiary carboxamides Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XWNBYCLNUZWIKB-AVKWCDSFSA-N (4-nitrophenyl)methyl (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)CC1=CC=CC=C1 XWNBYCLNUZWIKB-AVKWCDSFSA-N 0.000 description 1
- ABTUPEBOWRKQLD-SBXXRYSUSA-N (4-nitrophenyl)methyl (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@H]1N2C(C1N)=O)CC(C)=C2C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 ABTUPEBOWRKQLD-SBXXRYSUSA-N 0.000 description 1
- DBLJWHPZEGMNDK-AFYYWNPRSA-N (6R)-3-methyl-8-oxo-4-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O(C1=CC=CC=C1)CC(=O)NC1S[C@H]2N(C(=C1C)C(=O)O)C(C2)=O DBLJWHPZEGMNDK-AFYYWNPRSA-N 0.000 description 1
- NLZHNYNXJJFHRW-ZCFIWIBFSA-N (6r)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C[C@H]21 NLZHNYNXJJFHRW-ZCFIWIBFSA-N 0.000 description 1
- RKPYPVYWRWYHKC-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)COC1=CC=CC=C1 RKPYPVYWRWYHKC-WPZCJLIBSA-N 0.000 description 1
- CIPQGGYPCPIDBB-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 CIPQGGYPCPIDBB-WPZCJLIBSA-N 0.000 description 1
- PYEJPVLWBLJEPJ-JOPIAHFSSA-N (6r)-7-(1,3-dioxoisoindol-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C1=O)[C@@H]2N1C(C(O)=O)=C(C)CS2 PYEJPVLWBLJEPJ-JOPIAHFSSA-N 0.000 description 1
- NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 1
- ZSNWHUWUQPHFPR-UHFFFAOYSA-N 1,3-diphenyl-1-triethylsilylurea Chemical compound C=1C=CC=CC=1N([Si](CC)(CC)CC)C(=O)NC1=CC=CC=C1 ZSNWHUWUQPHFPR-UHFFFAOYSA-N 0.000 description 1
- OUYBHCPCSNUQHE-UHFFFAOYSA-N 1,3-diphenyl-1-trimethylsilylurea Chemical compound C=1C=CC=CC=1N([Si](C)(C)C)C(=O)NC1=CC=CC=C1 OUYBHCPCSNUQHE-UHFFFAOYSA-N 0.000 description 1
- OWBDCUQNIPFHOU-UHFFFAOYSA-N 1,3-diphenyl-1-triphenylsilylurea Chemical compound C=1C=CC=CC=1N([Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)NC1=CC=CC=C1 OWBDCUQNIPFHOU-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BDFJDTSVAXEUTD-FQNRMIAFSA-N 2,2,2-trichloroethyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)COC1=CC=CC=C1 BDFJDTSVAXEUTD-FQNRMIAFSA-N 0.000 description 1
- HTVAZIIPZPMPPD-UHFFFAOYSA-N 2,2,2-trifluoro-N-triphenylsilylacetamide Chemical compound FC(C(=O)N[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F HTVAZIIPZPMPPD-UHFFFAOYSA-N 0.000 description 1
- XDDNSKIZKRPPPN-UHFFFAOYSA-N 2,2,2-trifluoro-N-tripropylsilylacetamide Chemical compound C(CC)[Si](CCC)(CCC)NC(C(F)(F)F)=O XDDNSKIZKRPPPN-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GVHIREZHTRULPT-UHFFFAOYSA-N 2-methyl-n-trimethylsilylpropan-2-amine Chemical compound CC(C)(C)N[Si](C)(C)C GVHIREZHTRULPT-UHFFFAOYSA-N 0.000 description 1
- GLZLPIBNJAQHFD-UHFFFAOYSA-N 2-methyl-n-tripropylsilylpropan-2-amine Chemical compound CCC[Si](CCC)(CCC)NC(C)(C)C GLZLPIBNJAQHFD-UHFFFAOYSA-N 0.000 description 1
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- REJURGCORCWNQR-UHFFFAOYSA-N C(C)C(C[SiH2]Cl)(CC)CC Chemical compound C(C)C(C[SiH2]Cl)(CC)CC REJURGCORCWNQR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DQZBQISVRWDOLR-PDLYCEKZSA-N [N+](=O)([O-])C1=CC=C(CC2C(S([C@H]3N2C(C3NC(COC3=CC=CC=C3)=O)=O)=O)(C)C)C=C1 Chemical compound [N+](=O)([O-])C1=CC=C(CC2C(S([C@H]3N2C(C3NC(COC3=CC=CC=C3)=O)=O)=O)(C)C)C=C1 DQZBQISVRWDOLR-PDLYCEKZSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- MHWVMMHIJHHXQP-UHFFFAOYSA-N benzene-1,2,3-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O MHWVMMHIJHHXQP-UHFFFAOYSA-N 0.000 description 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
- MTRNNCLQPVCDLF-UHFFFAOYSA-N benzyl-[2-(benzylazaniumyl)ethyl]azanium;diacetate Chemical compound CC(O)=O.CC(O)=O.C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 MTRNNCLQPVCDLF-UHFFFAOYSA-N 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- RLECCBFNWDXKPK-UHFFFAOYSA-N bis(trimethylsilyl)sulfide Chemical compound C[Si](C)(C)S[Si](C)(C)C RLECCBFNWDXKPK-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- QZQQBWVFOFYUBV-UHFFFAOYSA-N cyclobutanesulfonic acid Chemical compound OS(=O)(=O)C1CCC1 QZQQBWVFOFYUBV-UHFFFAOYSA-N 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- YAIKGZQRXQYYJZ-UHFFFAOYSA-N cyclopentanesulfonic acid Chemical compound OS(=O)(=O)C1CCCC1 YAIKGZQRXQYYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MAZKNBXUMANNDL-UHFFFAOYSA-M lithium;2-ethylhexanoate Chemical compound [Li+].CCCCC(CC)C([O-])=O MAZKNBXUMANNDL-UHFFFAOYSA-M 0.000 description 1
- GKQWYZBANWAFMQ-UHFFFAOYSA-M lithium;2-hydroxypropanoate Chemical compound [Li+].CC(O)C([O-])=O GKQWYZBANWAFMQ-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IBEWLPMHOLLARQ-UHFFFAOYSA-N n-ethyl-n-triethylsilylacetamide Chemical compound CCN(C(C)=O)[Si](CC)(CC)CC IBEWLPMHOLLARQ-UHFFFAOYSA-N 0.000 description 1
- ZTAJIYKRQQZJJH-UHFFFAOYSA-N n-methyl-n-triethylsilylmethanamine Chemical compound CC[Si](CC)(CC)N(C)C ZTAJIYKRQQZJJH-UHFFFAOYSA-N 0.000 description 1
- QHUOBLDKFGCVCG-UHFFFAOYSA-N n-methyl-n-trimethylsilylacetamide Chemical compound CC(=O)N(C)[Si](C)(C)C QHUOBLDKFGCVCG-UHFFFAOYSA-N 0.000 description 1
- WSFGZBVVUSQSHW-UHFFFAOYSA-N n-methyl-n-triphenylsilylacetamide Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(N(C(C)=O)C)C1=CC=CC=C1 WSFGZBVVUSQSHW-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BDXVCEVTRGKUJZ-UHFFFAOYSA-N n-tributylsilylacetamide Chemical compound CCCC[Si](CCCC)(CCCC)NC(C)=O BDXVCEVTRGKUJZ-UHFFFAOYSA-N 0.000 description 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 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000944 sulfenic acid group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- QPHQCJNOZBWLDN-UHFFFAOYSA-N triethyl(triethylsilylsulfanyl)silane Chemical compound CC[Si](CC)(CC)S[Si](CC)(CC)CC QPHQCJNOZBWLDN-UHFFFAOYSA-N 0.000 description 1
- YKPHTSHERCDMCL-UHFFFAOYSA-N trimethyl(prop-1-enoxy)silane Chemical compound CC=CO[Si](C)(C)C YKPHTSHERCDMCL-UHFFFAOYSA-N 0.000 description 1
- NTJPIRDYMVYFNP-UHFFFAOYSA-M trimethylsilylmethanesulfonate Chemical compound C[Si](C)(C)CS([O-])(=O)=O NTJPIRDYMVYFNP-UHFFFAOYSA-M 0.000 description 1
- ISCKYXPBDFZWGV-UHFFFAOYSA-N triphenyl(prop-1-enoxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC=CC)C1=CC=CC=C1 ISCKYXPBDFZWGV-UHFFFAOYSA-N 0.000 description 1
- RVIJNLNRLUDHEM-UHFFFAOYSA-N triphenylsilyl propane-1-sulfonate Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OS(=O)(=O)CCC)C1=CC=CC=C1 RVIJNLNRLUDHEM-UHFFFAOYSA-N 0.000 description 1
- KHQZLUVCZCAMFU-UHFFFAOYSA-N tripropyl(tripropylsilyloxy)silane Chemical compound CCC[Si](CCC)(CCC)O[Si](CCC)(CCC)CCC KHQZLUVCZCAMFU-UHFFFAOYSA-N 0.000 description 1
- WNOZBPBPOQKGLP-UHFFFAOYSA-N tripropylsilyl ethanesulfonate Chemical compound CCC[Si](CCC)(CCC)OS(=O)(=O)CC WNOZBPBPOQKGLP-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
-
- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS773703A CS197218B2 (cs) | 1972-05-10 | 1977-06-06 | Způsob výroby nových silylesterů azetidin-2-sulíenátů |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25207872A | 1972-05-10 | 1972-05-10 | |
| US05/349,876 US3944545A (en) | 1972-05-10 | 1973-04-12 | Process for preparing desacetoxycephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197217B2 true CS197217B2 (en) | 1980-04-30 |
Family
ID=26942026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS733319A CS197217B2 (en) | 1972-05-10 | 1973-05-10 | Method of conversion of penicilin sulphoxide into deacetoxy cephalosporin and lithium salt of the same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3944545A (no) |
| JP (2) | JPS5418276B2 (no) |
| AR (1) | AR203722A1 (no) |
| AT (1) | AT333424B (no) |
| AU (1) | AU476568B2 (no) |
| BG (2) | BG20816A3 (no) |
| CA (1) | CA1026744A (no) |
| CH (2) | CH582187A5 (no) |
| CS (1) | CS197217B2 (no) |
| DD (2) | DD116617A5 (no) |
| DE (1) | DE2323395A1 (no) |
| ES (1) | ES414645A1 (no) |
| FR (1) | FR2184069B1 (no) |
| GB (1) | GB1412856A (no) |
| HU (2) | HU170406B (no) |
| IE (1) | IE38150B1 (no) |
| IL (1) | IL42148A (no) |
| NL (1) | NL7306500A (no) |
| PH (1) | PH14066A (no) |
| SE (2) | SE429046B (no) |
| YU (1) | YU36925B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA732972B (en) * | 1972-05-10 | 1974-11-27 | Lilly Co Eli | Process for preparing desacetoxycephalosporins and novel intermediates |
| 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 |
| US4159266A (en) * | 1974-12-24 | 1979-06-26 | Eli Lilly And Company | Method of preparation of 3-methylenecephams |
| AT342197B (de) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | Neues verfahren zur herstellung von 3-cephemverbindungen |
| JPS5214789A (en) * | 1975-07-22 | 1977-02-03 | Shionogi & Co Ltd | Process for preparing 3-substiuted cephem compounds by ring closure |
| US4536334A (en) * | 1979-06-28 | 1985-08-20 | Sumitomo Chemical Company, Limited | Preparation of β-lactam derivatives |
| US5302713A (en) * | 1992-03-31 | 1994-04-12 | Industrial Technology Research Institute | Method for the preparation of Δ3 -7-substituted amino desacetoxy cephalosporanic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591585A (en) * | 1969-02-14 | 1971-07-06 | Lilly Co Eli | Process for making desacetoxycephalosporins |
| US3819622A (en) * | 1969-03-11 | 1974-06-25 | Glaxo Lab Ltd | Method of producing 7beta-acylamido-3-methylceph-3-em-4-carboxylic acid esters |
| FR2037858A5 (no) * | 1969-03-11 | 1970-12-31 | Glaxo Lab Ltd | |
| GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1973
- 1973-04-12 US US05/349,876 patent/US3944545A/en not_active Expired - Lifetime
- 1973-04-30 GB GB2034873A patent/GB1412856A/en not_active Expired
- 1973-04-30 IL IL42148A patent/IL42148A/en unknown
- 1973-05-03 CA CA170,357A patent/CA1026744A/en not_active Expired
- 1973-05-03 AU AU55197/73A patent/AU476568B2/en not_active Expired
- 1973-05-07 IE IE717/73A patent/IE38150B1/xx unknown
- 1973-05-08 HU HUEI561A patent/HU170406B/hu unknown
- 1973-05-08 HU HUEI475A patent/HU166698B/hu unknown
- 1973-05-09 CH CH654773A patent/CH582187A5/xx not_active IP Right Cessation
- 1973-05-09 AT AT410573A patent/AT333424B/de not_active IP Right Cessation
- 1973-05-09 SE SE7306497A patent/SE429046B/xx unknown
- 1973-05-09 NL NL7306500A patent/NL7306500A/xx not_active Application Discontinuation
- 1973-05-09 DE DE2323395A patent/DE2323395A1/de not_active Withdrawn
- 1973-05-09 YU YU1219/73A patent/YU36925B/xx unknown
- 1973-05-10 DD DD180331*A patent/DD116617A5/xx unknown
- 1973-05-10 BG BG023570A patent/BG20816A3/xx unknown
- 1973-05-10 JP JP5204773A patent/JPS5418276B2/ja not_active Expired
- 1973-05-10 DD DD170755A patent/DD108302A5/xx unknown
- 1973-05-10 PH PH14603A patent/PH14066A/en unknown
- 1973-05-10 CS CS733319A patent/CS197217B2/cs unknown
- 1973-05-10 AR AR247948A patent/AR203722A1/es active
- 1973-05-10 FR FR7316915A patent/FR2184069B1/fr not_active Expired
- 1973-05-10 ES ES414645A patent/ES414645A1/es not_active Expired
- 1973-05-10 BG BG027289A patent/BG20380A3/xx unknown
-
1976
- 1976-03-29 CH CH654773A patent/CH580638A5/xx not_active IP Right Cessation
- 1976-04-15 SE SE7604463A patent/SE429968B/xx not_active IP Right Cessation
-
1978
- 1978-07-28 JP JP53092451A patent/JPS585917B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU476568B2 (en) | 1976-09-30 |
| AU5519773A (en) | 1974-11-07 |
| BG20816A3 (bg) | 1975-12-20 |
| BG20380A3 (bg) | 1975-11-05 |
| SE429046B (sv) | 1983-08-08 |
| YU36925B (en) | 1984-08-31 |
| IE38150B1 (en) | 1978-01-04 |
| FR2184069A1 (no) | 1973-12-21 |
| CH580638A5 (no) | 1976-10-15 |
| JPS4947388A (no) | 1974-05-08 |
| AT333424B (de) | 1976-11-25 |
| NL7306500A (no) | 1973-11-13 |
| AR203722A1 (es) | 1975-10-15 |
| DE2323395A1 (de) | 1973-11-29 |
| CA1026744A (en) | 1978-02-21 |
| SE429968B (sv) | 1983-10-10 |
| DD108302A5 (no) | 1974-09-12 |
| HU166698B (no) | 1975-05-28 |
| IL42148A0 (en) | 1973-06-29 |
| CH582187A5 (no) | 1976-11-30 |
| IL42148A (en) | 1976-08-31 |
| JPS5418276B2 (no) | 1979-07-06 |
| DD116617A5 (no) | 1975-12-05 |
| US3944545A (en) | 1976-03-16 |
| GB1412856A (en) | 1975-11-05 |
| PH14066A (en) | 1981-01-26 |
| FR2184069B1 (no) | 1975-08-22 |
| JPS5444657A (en) | 1979-04-09 |
| ES414645A1 (es) | 1976-06-16 |
| HU170406B (en) | 1977-06-28 |
| SE7604463L (sv) | 1976-04-15 |
| IE38150L (en) | 1973-11-10 |
| ATA410573A (de) | 1976-03-15 |
| JPS585917B2 (ja) | 1983-02-02 |
| YU121973A (en) | 1982-06-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4631150A (en) | Process for the preparation of penems | |
| SE405857B (sv) | Forfarande for substituerande av en grupp i 6-resp 7-stellning hos en penicillansyraforening eller cefalosporansyraforening | |
| EP0043546B1 (en) | 7-oxo-cephalosporins and 6-oxo-penicillins, their analogues and process for their preparation | |
| CS197217B2 (en) | Method of conversion of penicilin sulphoxide into deacetoxy cephalosporin and lithium salt of the same | |
| US4683303A (en) | Reduction process for the preparation of 4-unsubstituted azetidin-2-ones | |
| JPH0146516B2 (no) | ||
| US4145540A (en) | 7β-Phosphoramido-7α-methoxycephalosporanic acid derivatives | |
| FI75165C (fi) | Foerbaettrat foerfarande foer framstaellning av penicillansyraklormetylestrar. | |
| US4051132A (en) | Process for epimerizing beta-lactam antibiotic compounds by means of an acid quench | |
| EP0022326B1 (en) | Process for chemically removing the acyl sidechain from cephalosporins and penicillins | |
| US4138553A (en) | 3-Methylene cephalosporanic acid derivatives and process for preparation thereof | |
| US4771134A (en) | Ring-opening process for preparing azetidinone intermediates | |
| US4167630A (en) | Process for epimerizing beta-lactam antibiotic compounds, and related products | |
| US4675396A (en) | 7-Oxo-4-thia-1-azabicyclo(3,2,0)heptane derivatives | |
| US4379923A (en) | Preparation of 7-acylamino-3-(thio-substituted)-methyl 3-cephem-4-carboxylic acid-1-oxide derivatives | |
| KR880001990B1 (ko) | 페니실린과 세팔로스포린 화합물의 제조방법 및 이들의 제조에 사용한 새로운 중간체의 제조방법 | |
| US4159267A (en) | Novel silyl ester azetidine-2-sulfenate intermediates and process for preparing desacetoxycephalosporins | |
| US4334065A (en) | Cephalosporin intermediates | |
| PL172378B1 (pl) | Sposób wytwarzania nowych 4-podstawionych azetydynonów PL PL PL PL PL PL | |
| JPH0247996B2 (no) | ||
| US4447602A (en) | Process to prepare 7-substituted cephalosporins or 6-substituted penicillins | |
| US3962226A (en) | 3-nitrooxycepham compounds and process for preparing desacetoxycephalosporins therefrom | |
| CA1066268A (en) | Process for preparing 3-acyloxymethyl-2-cephem compounds | |
| US4115383A (en) | Alkoxycarbonyl-ethylthio-azetidinones and process for their preparation | |
| EP0136177A2 (en) | 3-Azidocephalosporins as intermediates and novel antibacterial agents |