NL8005041A - Werkwijze voor de bereiding van thioethers, alsmede gesilyleerde thiolen voor toepassing bij deze werkwijze. - Google Patents
Werkwijze voor de bereiding van thioethers, alsmede gesilyleerde thiolen voor toepassing bij deze werkwijze. Download PDFInfo
- Publication number
- NL8005041A NL8005041A NL8005041A NL8005041A NL8005041A NL 8005041 A NL8005041 A NL 8005041A NL 8005041 A NL8005041 A NL 8005041A NL 8005041 A NL8005041 A NL 8005041A NL 8005041 A NL8005041 A NL 8005041A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- groups
- alkyl
- carbon atoms
- substituted
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 150000003573 thiols Chemical class 0.000 title claims description 29
- 150000003568 thioethers Chemical class 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 38
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 27
- -1 2-benzothiazolyl Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 11
- 229940081974 saccharin Drugs 0.000 claims description 11
- 235000019204 saccharin Nutrition 0.000 claims description 11
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 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 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- DOOAJZCMASXUKA-UHFFFAOYSA-N trimethyl-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]silane Chemical compound CC1=NN=C(S[Si](C)(C)C)S1 DOOAJZCMASXUKA-UHFFFAOYSA-N 0.000 claims description 6
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- DGZBRVOXGIVBLN-UHFFFAOYSA-N [(diphenoxyphosphorylamino)-phenoxyphosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)NP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 DGZBRVOXGIVBLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 3
- RLFZYIUUQBHRNV-UHFFFAOYSA-N 2,5-dihydrooxadiazole Chemical compound C1ONN=C1 RLFZYIUUQBHRNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- IOLZPCPQAGFTEY-QRWNGCHQSA-N (6r)-7-amino-3-methyl-5,8-dioxo-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class O=S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@H]21 IOLZPCPQAGFTEY-QRWNGCHQSA-N 0.000 claims description 2
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 claims description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- FGXOGRSGUNCHQL-UHFFFAOYSA-N 2,2,2-trichloro-n-dimethoxyphosphorylacetamide Chemical compound COP(=O)(OC)NC(=O)C(Cl)(Cl)Cl FGXOGRSGUNCHQL-UHFFFAOYSA-N 0.000 claims description 2
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- SGJFNRQZMRIAJP-UHFFFAOYSA-N n-(4-methylphenyl)sulfonylbenzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1 SGJFNRQZMRIAJP-UHFFFAOYSA-N 0.000 claims description 2
- ZBGWAJQUDSCDPB-UHFFFAOYSA-N n-(benzenesulfonyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ZBGWAJQUDSCDPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- SVWAHAPZUQYXGM-UHFFFAOYSA-N (4-oxo-3h-phthalazin-1-yl) benzoate Chemical compound N=1NC(=O)C2=CC=CC=C2C=1OC(=O)C1=CC=CC=C1 SVWAHAPZUQYXGM-UHFFFAOYSA-N 0.000 claims 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
- JHWLSKLAWGZYSO-UHFFFAOYSA-N 2-methoxy-n-methylsulfonylnaphthalene-1-carboxamide Chemical compound C1=CC=CC2=C(C(=O)NS(C)(=O)=O)C(OC)=CC=C21 JHWLSKLAWGZYSO-UHFFFAOYSA-N 0.000 claims 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 229930186147 Cephalosporin Natural products 0.000 abstract description 3
- 229940124587 cephalosporin Drugs 0.000 abstract description 3
- 150000001780 cephalosporins Chemical class 0.000 abstract description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RHJOXSLOFJOBMY-UHFFFAOYSA-N trimethyl-(5-trimethylsilylsulfanyltriazol-1-yl)silane Chemical compound C[Si](C)(C)SC1=CN=NN1[Si](C)(C)C RHJOXSLOFJOBMY-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- HHGMADGROXARPN-UHFFFAOYSA-M sodium;2h-triazole-4-thiolate Chemical compound [Na+].[S-]C=1C=NNN=1 HHGMADGROXARPN-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- CSZHCBOEEPVSDP-UHFFFAOYSA-N (2-nitro-N-(2,2,2-trichloroacetyl)anilino)phosphonic acid Chemical compound C1=CC=C(C(=C1)N(C(=O)C(Cl)(Cl)Cl)P(=O)(O)O)[N+](=O)[O-] CSZHCBOEEPVSDP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical compound C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012088 reference solution Substances 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- SDXAAZSIHFTITI-GVMQWFMMSA-N trimethylsilyl (6r)-3-(bromomethyl)-5,8-dioxo-7-[(2-phenylacetyl)amino]-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2S(=O)CC(CBr)=C(N2C1=O)C(=O)O[Si](C)(C)C)NC(=O)CC1=CC=CC=C1 SDXAAZSIHFTITI-GVMQWFMMSA-N 0.000 description 2
- PHIMLNXVWFHTLQ-MYXBAGLQSA-N (6r)-3-methyl-5,8-dioxo-7-[(2-phenylacetyl)amino]-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2=O)C)C(O)=O)NC(=O)CC1=CC=CC=C1 PHIMLNXVWFHTLQ-MYXBAGLQSA-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 class S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 1
- FAEFDCDBPXCRKX-UHFFFAOYSA-N (sulfonylamino)phosphonic acid Chemical class OP(O)(=O)N=S(=O)=O FAEFDCDBPXCRKX-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- QARMHFWUIWEIOX-UHFFFAOYSA-N 2-methoxy-n-(4-methylphenyl)sulfonylnaphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QARMHFWUIWEIOX-UHFFFAOYSA-N 0.000 description 1
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 description 1
- LPUUYZVKCMCHLO-UHFFFAOYSA-N 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(=O)C2=C1Cl LPUUYZVKCMCHLO-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 description 1
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical class S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- UKRQQTUHXSUNPV-UHFFFAOYSA-N N1NNN=CC1 Chemical compound N1NNN=CC1 UKRQQTUHXSUNPV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- DOLYPOKJFDZUEJ-UHFFFAOYSA-M potassium;5-methyl-1,3,4-thiadiazole-2-thiolate Chemical compound [K+].CC1=NN=C([S-])S1 DOLYPOKJFDZUEJ-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- JCEZYJSPNBDMTK-UHFFFAOYSA-N trimethyl-(1-methyltetrazol-5-yl)sulfanylsilane Chemical compound CN1N=NN=C1S[Si](C)(C)C JCEZYJSPNBDMTK-UHFFFAOYSA-N 0.000 description 1
- JGAMHGKSASEHSH-UHFFFAOYSA-N trimethyl-(3-trimethylsilylsulfanyl-1,2,4-triazol-1-yl)silane Chemical compound C[Si](C)(C)SC=1N=CN([Si](C)(C)C)N=1 JGAMHGKSASEHSH-UHFFFAOYSA-N 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- C07F7/0801—General processes
-
- 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
- C07F7/0898—Compounds with a Si-S linkage
-
- 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
-
- 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
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8005041A NL8005041A (nl) | 1980-09-05 | 1980-09-05 | Werkwijze voor de bereiding van thioethers, alsmede gesilyleerde thiolen voor toepassing bij deze werkwijze. |
| IL63100A IL63100A0 (en) | 1980-07-04 | 1981-06-15 | Trimethylsilylation of organic compounds and certain trimethylsilylated thiols obtained thereby |
| AU71886/81A AU543108B2 (en) | 1980-07-04 | 1981-06-16 | New catalysts for silylation |
| PT73261A PT73261B (en) | 1980-07-04 | 1981-06-25 | New catalysts for silylation |
| FI812094A FI81776C (fi) | 1980-07-04 | 1981-07-02 | Foerfarande foer trimetylsilylering av organiska foereningar innehaollande en eller flera aktiva vaeteatomer medelst hexametyldisilazan. |
| GR65410A GR74366B (el) | 1980-07-04 | 1981-07-02 | |
| HU811958A HU185935B (en) | 1980-07-04 | 1981-07-03 | Process for sililizing organic materials with 1,1,1-trimethyl-n-bracket-trimethyl-silyl-bracket closed-silanamine in the presence of catalyty containing nitrogen |
| CA000381119A CA1184556A (en) | 1980-07-04 | 1981-07-03 | Catalysts for silylation |
| DK296781A DK166581C (da) | 1980-07-04 | 1981-07-03 | Fremgangsmaade til trimethylsilylering af organiske forbindelser med hexamethyldisilazan i naervaerelse af en katalysator |
| ES503650A ES8301485A1 (es) | 1980-07-04 | 1981-07-03 | Procedimiento para la trimetilsililacion de compuestos organicos que llevan uno o mas atomo de hidrogeno activo. |
| NO812275A NO812275L (no) | 1980-07-04 | 1981-07-03 | Fremgangsmaate for sililering av organiske forbindelser |
| EP81200771A EP0043630B1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| DE8181200771T DE3173428D1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| AT81200771T ATE17353T1 (de) | 1980-07-04 | 1981-07-03 | Verfahren zum silylieren organischer verbindungen mit 1,1,1-trimethyl-n-(trimethylsilyl)silanamin mit hilfe von katalysatoren mit gewissen stickstoffhaltigen verbindungen. |
| IE1495/81A IE51452B1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| US06/280,350 US4400509A (en) | 1980-07-04 | 1981-07-06 | Silylation process |
| AU74345/81A AU540377B2 (en) | 1980-09-05 | 1981-08-19 | Preparation of 7-acyl-amino-3-(thio-substituted)methyl- 3-cephem-4-carboxylic acid 1-oxide derivatives |
| IL63615A IL63615A0 (en) | 1980-09-05 | 1981-08-19 | Preparation of 7-acylamino-3-(thiosubstituted)methyl-3-cephem-4-carboxylic acid 1-oxide derivatives |
| US06/297,214 US4379923A (en) | 1980-09-05 | 1981-08-28 | Preparation of 7-acylamino-3-(thio-substituted)-methyl 3-cephem-4-carboxylic acid-1-oxide derivatives |
| DE8181200981T DE3169840D1 (en) | 1980-09-05 | 1981-09-02 | Process for the preparation of 7-acylamino-3-(thio-substituted)methyl-3-cephem-4-carboxylic acid 1-oxide derivatives |
| AT81200981T ATE12644T1 (de) | 1980-09-05 | 1981-09-02 | Verfahren zur herstellung von 7-acylamino-3-(thio substituierte)methyl-3-cephem-4-carboxylsaeure-1 oxyd-verbindungen. |
| PT73615A PT73615B (en) | 1980-09-05 | 1981-09-02 | Process for the preparation of 7-acylamino-3-(thio-substitud) methyl-3-cephem-4-carboxylic acid 1-oxide derivatives |
| EP81200981A EP0047560B1 (en) | 1980-09-05 | 1981-09-02 | Process for the preparation of 7-acylamino-3-(thio-substituted)methyl-3-cephem-4-carboxylic acid 1-oxide derivatives |
| GR65943A GR75764B (el) | 1980-09-05 | 1981-09-03 | |
| JP56139208A JPS5780389A (en) | 1980-09-05 | 1981-09-03 | Manufacture of 7-acylamino-3-(thio substituted)methyl-3-cephem-4-carboxylic acid 1-oxide derivative |
| DK390281A DK162602C (da) | 1980-09-05 | 1981-09-03 | Fremgangsmaade til fremstilling af 7-acylamino-3-(thio-substitueret)methyl-3-cephem-4-carboxylsyre-1-oxid-derivater |
| HU812550A HU185311B (en) | 1980-09-05 | 1981-09-03 | Process for producing 7-acylamino-3-bracket-thio-substituted-bracket closed-methyl-3-cephema-4-carboxylic acid-1-oxide derivatives |
| CA000385192A CA1176241A (en) | 1980-09-05 | 1981-09-03 | Process for the preparation of 7-acylamino-3-(thio- substituted)methyl-3-cephem-4-carboxylic acid 1- oxide derivatives |
| NO812990A NO160004C (no) | 1980-09-05 | 1981-09-03 | Fremgangsmaate for fremstilling av 7-acylamino-3-(tiosubstituerte)metyl-3-cefem-4-karboksylsyre-1-oksyd-derivater. |
| KR1019810003284A KR860000283B1 (ko) | 1980-09-05 | 1981-09-03 | 7-아실아미노-3-(티오-치환)메틸-3-세펨-4-카르복시산 1-옥시드 유도체류의 제조방법 |
| FI812724A FI73438C (fi) | 1980-09-05 | 1981-09-03 | Foerfarande foer framstaellning av 7-acylamino-3-(tiosubstituerad)metyl-3-cefem-4-karboxylsyra-1-oxid derivat. |
| ES505208A ES8206536A1 (es) | 1980-09-05 | 1981-09-04 | Procedimiento para preparar derivados de 1-oxido de acido 7-acilamino-3-(tio-sustituido)metil-3-cefem-4-carboxilico |
| IE2046/81A IE51545B1 (en) | 1980-09-05 | 1981-09-04 | Process for the preparation of 7-acylamino-3-(thio-substituted)methyl-3-cephem-4-carboxylic acid 1-oxide derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8005041A NL8005041A (nl) | 1980-09-05 | 1980-09-05 | Werkwijze voor de bereiding van thioethers, alsmede gesilyleerde thiolen voor toepassing bij deze werkwijze. |
| NL8005041 | 1980-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8005041A true NL8005041A (nl) | 1982-04-01 |
Family
ID=19835841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8005041A NL8005041A (nl) | 1980-07-04 | 1980-09-05 | Werkwijze voor de bereiding van thioethers, alsmede gesilyleerde thiolen voor toepassing bij deze werkwijze. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4379923A (el) |
| EP (1) | EP0047560B1 (el) |
| JP (1) | JPS5780389A (el) |
| KR (1) | KR860000283B1 (el) |
| AT (1) | ATE12644T1 (el) |
| AU (1) | AU540377B2 (el) |
| CA (1) | CA1176241A (el) |
| DE (1) | DE3169840D1 (el) |
| DK (1) | DK162602C (el) |
| ES (1) | ES8206536A1 (el) |
| FI (1) | FI73438C (el) |
| GR (1) | GR75764B (el) |
| HU (1) | HU185311B (el) |
| IE (1) | IE51545B1 (el) |
| IL (1) | IL63615A0 (el) |
| NL (1) | NL8005041A (el) |
| NO (1) | NO160004C (el) |
| PT (1) | PT73615B (el) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088831A1 (en) * | 1982-03-11 | 1983-09-21 | Gist-Brocades N.V. | Process for the preparation of thioethers |
| WO1996004286A1 (en) * | 1994-08-02 | 1996-02-15 | The Procter & Gamble Company | Process for making quinolonyl lactam antimicrobials and novel intermediate compounds |
| WO1996004247A1 (en) * | 1994-08-02 | 1996-02-15 | The Procter & Gamble Company | Process for making antimicrobial compounds |
| FR2794751B1 (fr) | 1999-06-08 | 2001-08-10 | Atofina | Procede de fabrication d'urees bis-silylees |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1241657A (en) * | 1967-08-21 | 1971-08-04 | Glaxo Lab Ltd | Improvements in or relating to cephalosporin compounds |
| GB1326531A (en) * | 1969-08-26 | 1973-08-15 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4148817A (en) * | 1976-03-25 | 1979-04-10 | Eli Lilly And Company | Process and intermediates for preparing cephalosporin antibiotics |
| US4129731A (en) * | 1976-12-08 | 1978-12-12 | E. R. Squibb & Sons, Inc. | Process for converting 3-methylene cephalosporins to 3-heterothiomethyl cephalosporins |
| US4284766A (en) * | 1978-09-21 | 1981-08-18 | Glaxo Group Limited | Process for the preparation of cephalosporin compounds |
| US4266049A (en) * | 1980-02-20 | 1981-05-05 | Eli Lilly And Company | Process for 3-iodomethyl cephalosporins |
-
1980
- 1980-09-05 NL NL8005041A patent/NL8005041A/nl not_active Application Discontinuation
-
1981
- 1981-08-19 AU AU74345/81A patent/AU540377B2/en not_active Ceased
- 1981-08-19 IL IL63615A patent/IL63615A0/xx not_active IP Right Cessation
- 1981-08-28 US US06/297,214 patent/US4379923A/en not_active Expired - Fee Related
- 1981-09-02 EP EP81200981A patent/EP0047560B1/en not_active Expired
- 1981-09-02 DE DE8181200981T patent/DE3169840D1/de not_active Expired
- 1981-09-02 PT PT73615A patent/PT73615B/pt not_active IP Right Cessation
- 1981-09-02 AT AT81200981T patent/ATE12644T1/de not_active IP Right Cessation
- 1981-09-03 KR KR1019810003284A patent/KR860000283B1/ko active
- 1981-09-03 GR GR65943A patent/GR75764B/el unknown
- 1981-09-03 DK DK390281A patent/DK162602C/da not_active IP Right Cessation
- 1981-09-03 HU HU812550A patent/HU185311B/hu not_active IP Right Cessation
- 1981-09-03 JP JP56139208A patent/JPS5780389A/ja active Granted
- 1981-09-03 NO NO812990A patent/NO160004C/no unknown
- 1981-09-03 CA CA000385192A patent/CA1176241A/en not_active Expired
- 1981-09-03 FI FI812724A patent/FI73438C/fi not_active IP Right Cessation
- 1981-09-04 ES ES505208A patent/ES8206536A1/es not_active Expired
- 1981-09-04 IE IE2046/81A patent/IE51545B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE51545B1 (en) | 1987-01-07 |
| IE812046L (en) | 1982-03-05 |
| DK162602B (da) | 1991-11-18 |
| AU7434581A (en) | 1982-03-11 |
| AU540377B2 (en) | 1984-11-15 |
| HU185311B (en) | 1985-01-28 |
| NO160004C (no) | 1989-03-01 |
| US4379923A (en) | 1983-04-12 |
| PT73615B (en) | 1982-11-16 |
| NO812990L (no) | 1982-03-08 |
| ES505208A0 (es) | 1982-08-16 |
| NO160004B (no) | 1988-11-21 |
| EP0047560A2 (en) | 1982-03-17 |
| DK162602C (da) | 1992-05-11 |
| PT73615A (en) | 1981-10-01 |
| KR860000283B1 (ko) | 1986-03-26 |
| ATE12644T1 (de) | 1985-04-15 |
| EP0047560B1 (en) | 1985-04-10 |
| FI812724L (fi) | 1982-03-06 |
| IL63615A0 (en) | 1981-11-30 |
| JPS5780389A (en) | 1982-05-19 |
| DE3169840D1 (en) | 1985-05-15 |
| DK390281A (da) | 1982-03-06 |
| KR830007687A (ko) | 1983-11-04 |
| CA1176241A (en) | 1984-10-16 |
| FI73438B (fi) | 1987-06-30 |
| EP0047560A3 (en) | 1982-12-01 |
| ES8206536A1 (es) | 1982-08-16 |
| FI73438C (fi) | 1987-10-09 |
| JPH0133106B2 (el) | 1989-07-11 |
| GR75764B (el) | 1984-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |