JPH0355475B2 - - Google Patents
Info
- Publication number
- JPH0355475B2 JPH0355475B2 JP57147268A JP14726882A JPH0355475B2 JP H0355475 B2 JPH0355475 B2 JP H0355475B2 JP 57147268 A JP57147268 A JP 57147268A JP 14726882 A JP14726882 A JP 14726882A JP H0355475 B2 JPH0355475 B2 JP H0355475B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- solution
- mmol
- minutes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 88
- -1 diazobutyrate compound Chemical class 0.000 claims description 56
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical group S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000006713 insertion reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 71
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 238000003756 stirring Methods 0.000 description 30
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000012267 brine Substances 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 150000001336 alkenes Chemical group 0.000 description 17
- 239000005457 ice water Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- AKCHDWZTAZCJLQ-UHFFFAOYSA-N ethyl 3-[tert-butyl(dimethyl)silyl]oxy-2-[tert-butyl(dimethyl)silyl]oxyiminobut-3-enoate Chemical compound CC(C)(C)[Si](C)(C)ON=C(C(=O)OCC)C(=C)O[Si](C)(C)C(C)(C)C AKCHDWZTAZCJLQ-UHFFFAOYSA-N 0.000 description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FHSRJJGTLZGBKD-UHFFFAOYSA-N benzhydryl 4-bromo-3-oxobutanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CC(=O)CBr)C1=CC=CC=C1 FHSRJJGTLZGBKD-UHFFFAOYSA-N 0.000 description 6
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N ethyl but-2-enoate Chemical compound CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 5
- 150000002440 hydroxy compounds Chemical class 0.000 description 5
- 150000002923 oximes Chemical group 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- QXNSHVVNEOAAOF-RXMQYKEDSA-N (6R)-4-oxa-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1OC=CN2[C@H]1CC2=O QXNSHVVNEOAAOF-RXMQYKEDSA-N 0.000 description 2
- AKFXQYMORAUSBD-UHFFFAOYSA-N 1-chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile Chemical compound C12=CC=CC=C2N=C2N1C(Cl)=CC(C)=C2C#N AKFXQYMORAUSBD-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- PLMCCOPFYJURPS-UHFFFAOYSA-N 4-bromo-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CBr PLMCCOPFYJURPS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CHKQALUEEULCPZ-UHFFFAOYSA-N amino 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)ON)C(C)=C1 CHKQALUEEULCPZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- MGDWUTQKXCZNAJ-UHFFFAOYSA-N ethyl 4-bromo-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CBr MGDWUTQKXCZNAJ-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 102100034195 Thrombopoietin Human genes 0.000 description 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000004718 beta keto acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- IACSYDRIOYGJNH-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(C)=O IACSYDRIOYGJNH-UHFFFAOYSA-N 0.000 description 1
- KLEXCBCJJFQFDW-UHFFFAOYSA-N ethyl 4-[tert-butyl(dimethyl)silyl]-2-[tert-butyl(dimethyl)silyl]oxyimino-3-oxobutanoate Chemical compound CC(C)(C)[Si](C)(C)ON=C(C(=O)OCC)C(=O)C[Si](C)(C)C(C)(C)C KLEXCBCJJFQFDW-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- BDMBWENRFFKJON-JWQCQUIFSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]hexadecanamide Chemical group CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 BDMBWENRFFKJON-JWQCQUIFSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- SYBXSZMNKDOUCA-UHFFFAOYSA-J rhodium(2+);tetraacetate Chemical compound [Rh+2].[Rh+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O SYBXSZMNKDOUCA-UHFFFAOYSA-J 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/21—Saturated compounds having only one carboxyl group and containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- C07C245/18—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- 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
- C07D205/085—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 nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-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
- C07F7/10—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57147268A JPS5936684A (ja) | 1982-08-24 | 1982-08-24 | １−オキサセフアム化合物の製造方法 |
| GR72205A GR78932B (Direct) | 1982-08-24 | 1983-08-12 | |
| US06/523,414 US4539148A (en) | 1982-08-24 | 1983-08-16 | Production of 1-oxacephams and intermediates |
| GB08322116A GB2126223B (en) | 1982-08-24 | 1983-08-17 | 4-substituted butyric acid derivatives |
| IE1936/83A IE55873B1 (en) | 1982-08-24 | 1983-08-18 | 4-substituted butyric acid derivatives |
| EP83401689A EP0102893B1 (en) | 1982-08-24 | 1983-08-19 | A novel production of 1-oxacephams |
| DE8383401689T DE3377276D1 (en) | 1982-08-24 | 1983-08-19 | A novel production of 1-oxacephams |
| IL69546A IL69546A (en) | 1982-08-24 | 1983-08-23 | 3-hydroxymethyl-3-butenoic acid derivatives,processes for their preparation and process for the preparation of antibacterial 1-oxacepham derivatives using them |
| DK385983A DK385983A (da) | 1982-08-24 | 1983-08-23 | Fremgangsmaade til fremstilling af 1-oxacephamer |
| HU832963A HU191875B (en) | 1982-08-24 | 1983-08-23 | Process for producing 7-alpha-/acyl-amino/-3-/exomethylene or oxo/-1-dethia-1-oxacephame-4-carboxylic acid esters |
| CA000435289A CA1227482A (en) | 1982-08-24 | 1983-08-24 | Production of l-oxacephams |
| KR1019830003960A KR900004149B1 (ko) | 1982-08-24 | 1983-08-24 | 1-옥사세팜 화합물의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57147268A JPS5936684A (ja) | 1982-08-24 | 1982-08-24 | １−オキサセフアム化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5936684A JPS5936684A (ja) | 1984-02-28 |
| JPH0355475B2 true JPH0355475B2 (Direct) | 1991-08-23 |
Family
ID=15426375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57147268A Granted JPS5936684A (ja) | 1982-08-24 | 1982-08-24 | １−オキサセフアム化合物の製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4539148A (Direct) |
| EP (1) | EP0102893B1 (Direct) |
| JP (1) | JPS5936684A (Direct) |
| KR (1) | KR900004149B1 (Direct) |
| CA (1) | CA1227482A (Direct) |
| DE (1) | DE3377276D1 (Direct) |
| DK (1) | DK385983A (Direct) |
| GB (1) | GB2126223B (Direct) |
| GR (1) | GR78932B (Direct) |
| HU (1) | HU191875B (Direct) |
| IE (1) | IE55873B1 (Direct) |
| IL (1) | IL69546A (Direct) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0115770B2 (en) * | 1983-01-07 | 1996-06-19 | Takeda Chemical Industries, Ltd. | Thiazole Derivatives |
| JPH0830051B2 (ja) * | 1986-05-21 | 1996-03-27 | 武田薬品工業株式会社 | ４−ハロゲノ−２−置換オキシイミノ−３−オキソ酪酸のエステルまたはアミドの製造法 |
| US4775745A (en) * | 1986-12-08 | 1988-10-04 | National Distillers And Chemical Corporation | Diazonium compounds useful as components for nucleic acid probes |
| GB8707515D0 (en) * | 1987-03-30 | 1987-05-07 | Fujisawa Pharmaceutical Co | Amino acid derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345081A (en) * | 1973-09-14 | 1974-01-30 | Lonza Ag | Process for the preparation of ypsilon-alkoxy-acetoacetic esters |
| US4011216A (en) * | 1975-04-11 | 1977-03-08 | Bristol-Myers Company | Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents |
| GB1533049A (en) * | 1976-04-15 | 1978-11-22 | Bristol Myers Canada Ltd | O-2-isocephem compounds and their preparation |
| JPS604811B2 (ja) * | 1976-07-28 | 1985-02-06 | 塩野義製薬株式会社 | メチルケトンのハロゲン化 |
| JPS5398951A (en) * | 1977-02-08 | 1978-08-29 | Shionogi & Co Ltd | Azetidinone derivatives and process for their preparation |
| CH649984A5 (de) * | 1981-06-17 | 1985-06-28 | Lonza Ag | 4-hydroxyacetessigsaeureethylester. |
| JPS58103391A (ja) * | 1981-12-11 | 1983-06-20 | Meiji Seika Kaisha Ltd | １−オキサデチア−セフエム誘導体の製造法 |
-
1982
- 1982-08-24 JP JP57147268A patent/JPS5936684A/ja active Granted
-
1983
- 1983-08-12 GR GR72205A patent/GR78932B/el unknown
- 1983-08-16 US US06/523,414 patent/US4539148A/en not_active Expired - Fee Related
- 1983-08-17 GB GB08322116A patent/GB2126223B/en not_active Expired
- 1983-08-18 IE IE1936/83A patent/IE55873B1/en not_active IP Right Cessation
- 1983-08-19 EP EP83401689A patent/EP0102893B1/en not_active Expired
- 1983-08-19 DE DE8383401689T patent/DE3377276D1/de not_active Expired
- 1983-08-23 HU HU832963A patent/HU191875B/hu not_active IP Right Cessation
- 1983-08-23 DK DK385983A patent/DK385983A/da not_active Application Discontinuation
- 1983-08-23 IL IL69546A patent/IL69546A/xx not_active IP Right Cessation
- 1983-08-24 CA CA000435289A patent/CA1227482A/en not_active Expired
- 1983-08-24 KR KR1019830003960A patent/KR900004149B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3377276D1 (en) | 1988-08-11 |
| EP0102893A1 (en) | 1984-03-14 |
| GB2126223A (en) | 1984-03-21 |
| KR900004149B1 (ko) | 1990-06-16 |
| IE55873B1 (en) | 1991-02-14 |
| DK385983D0 (da) | 1983-08-23 |
| DK385983A (da) | 1984-02-25 |
| CA1227482A (en) | 1987-09-29 |
| GR78932B (Direct) | 1984-10-02 |
| KR840005815A (ko) | 1984-11-19 |
| HU191875B (en) | 1987-04-28 |
| JPS5936684A (ja) | 1984-02-28 |
| IL69546A (en) | 1988-03-31 |
| IL69546A0 (en) | 1983-11-30 |
| GB2126223B (en) | 1986-06-04 |
| EP0102893B1 (en) | 1988-07-06 |
| US4539148A (en) | 1985-09-03 |
| IE831936L (en) | 1984-02-24 |
| GB8322116D0 (en) | 1983-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5874581A (en) | 2-silyloxy-tetrahydrothienopyridine, salt thereof and process for preparing the same | |
| JPWO1996011203A1 (ja) | ２−シリルオキシ−テトラヒドロチエノピリジン類、その塩およびその製造方法 | |
| JP3771566B2 (ja) | １−オキサセファロスポリン−７α−メトキシ−３−クロルメチル誘導体の製法 | |
| JP3717053B2 (ja) | プロスタサイクリン誘導体の立体選択的合成法 | |
| JPS5892672A (ja) | チアゾリン化合物およびその製造法 | |
| Gordon et al. | Sulfenyl transfer rearrangement of sulfenimines (thiooximes). A novel synthesis of 7. alpha.-methoxycephalosporins and 6. alpha.-methoxypenicillins | |
| US4443373A (en) | Process for the production of antibiotic penems | |
| JPH0246593B2 (Direct) | ||
| US5162524A (en) | Processes for making cephems from allenylazetidinone derivatives | |
| JPH0327554B2 (Direct) | ||
| US5162521A (en) | Processes for making cephems from allenylazetidinone derivatives | |
| US4845257A (en) | 4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives | |
| US5412091A (en) | 16-methyl-Δ1,4-pregnadiene-3,20-dione | |
| JPS6228786B2 (Direct) | ||
| EP0102893B1 (en) | A novel production of 1-oxacephams | |
| US4558124A (en) | Preparation of cephalosporin intermediate compounds | |
| US5266691A (en) | Processes for making cephems from allenylazetidinone derivatives | |
| EP0971919B1 (en) | Process for preparation of 4h-4-oxo-quinolizine-3-carboxylic acid derivatives | |
| US4640798A (en) | Intermediates for the preparation of penicillin and cephalosporin compounds | |
| US4235779A (en) | Bicyclic lactones | |
| JPH0558638B2 (Direct) | ||
| JPH0354110B2 (Direct) | ||
| JPH04279564A (ja) | スルホニル化合物およびビタミンａまたはそのエステルを製造する方法における中間体としての前記化合物使用 | |
| CA1240985A (en) | Preparation of cephalosporins | |
| JPS61100538A (ja) | 新規なシクロペンテンアルコ−ル類およびその製造法 |