CA1140554A - Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique - Google Patents

Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique

Info

Publication number: CA1140554A
Authority: CA; Canada
Prior art keywords: group; lower alkyl; phenyl; formula; amino
Prior art date: 1975-02-20
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

Application number

CA000344630A

Other languages

English (en)

Inventor

Robert B. Woodward

Hans Bickel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date 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 date listed.)

1975-02-20

Filing date

1980-01-29

Publication date

1983-02-01

1975-02-20 Priority claimed from CH215775A external-priority patent/CH626091A5/de

1975-08-25 Priority claimed from CH1096275A external-priority patent/CH627759A5/de

1976-02-18 Priority claimed from CA246,040A external-priority patent/CA1080695A/fr

1980-01-29 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1980-01-29 Priority to CA000344630A priority Critical patent/CA1140554A/fr

1983-02-01 Application granted granted Critical

1983-02-01 Publication of CA1140554A publication Critical patent/CA1140554A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
238000004519 manufacturing process Methods 0.000 title claims abstract description 17
230000008569 process Effects 0.000 title claims abstract description 17
RSKFUQVUEREZJB-DJWKRKHSSA-N (z)-2-(2-oxoazetidin-1-yl)but-2-enoic acid Chemical class C\C=C(C(O)=O)/N1CCC1=O RSKFUQVUEREZJB-DJWKRKHSSA-N 0.000 title description 2
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 34
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract description 4
-1 2-(2-oxoazetidin-1-yl)-crotonic acid compound Chemical class 0.000 claims description 612
125000000217 alkyl group Chemical group 0.000 claims description 123
125000003545 alkoxy group Chemical group 0.000 claims description 70
150000001875 compounds Chemical class 0.000 claims description 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 64
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 44
125000003118 aryl group Chemical group 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 39
150000002367 halogens Chemical class 0.000 claims description 37
125000002252 acyl group Chemical group 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
125000003277 amino group Chemical group 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 25
229910052801 chlorine Inorganic materials 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 24
229910001385 heavy metal Inorganic materials 0.000 claims description 23
125000000623 heterocyclic group Chemical group 0.000 claims description 21
239000007858 starting material Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 17
229910052783 alkali metal Inorganic materials 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 16
125000002541 furyl group Chemical group 0.000 claims description 15
125000001544 thienyl group Chemical group 0.000 claims description 15
125000004414 alkyl thio group Chemical group 0.000 claims description 14
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 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
125000001624 naphthyl group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000002950 monocyclic group Chemical group 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 9
125000001786 isothiazolyl group Chemical group 0.000 claims description 9
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 9
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
125000002619 bicyclic group Chemical group 0.000 claims description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
150000003335 secondary amines Chemical class 0.000 claims description 4
125000001302 tertiary amino group Chemical group 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000004468 heterocyclylthio group Chemical group 0.000 claims description 3
125000004149 thio group Chemical group *S* 0.000 claims description 3
125000003441 thioacyl group Chemical group 0.000 claims description 3
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 2
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
GSBVSWAYGAXPRF-FEZSWGLMSA-N (4-nitrophenyl)methyl (e)-3-(cyclohexylamino)-2-[2-(4-methylphenyl)sulfonylsulfanyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]but-2-enoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)SC1C(NC(=O)COC=2C=CC=CC=2)C(=O)N1\C(C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)=C(/C)NC1CCCCC1 GSBVSWAYGAXPRF-FEZSWGLMSA-N 0.000 claims 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
241000965481 Darksidea alpha Species 0.000 claims 1
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 39
150000002148 esters Chemical class 0.000 abstract description 16
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract description 4
150000007513 acids Chemical class 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
239000000243 solution Substances 0.000 description 62
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
150000003254 radicals Chemical class 0.000 description 61
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
125000001931 aliphatic group Chemical group 0.000 description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
229940073584 methylene chloride Drugs 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
235000017168 chlorine Nutrition 0.000 description 24
229940060038 chlorine Drugs 0.000 description 24
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
230000000875 corresponding effect Effects 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
239000004215 Carbon black (E152) Substances 0.000 description 21
229930195733 hydrocarbon Natural products 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
125000004423 acyloxy group Chemical group 0.000 description 15
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
238000002329 infrared spectrum Methods 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
125000004442 acylamino group Chemical group 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000047 product Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
125000002947 alkylene group Chemical group 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
229960001407 sodium bicarbonate Drugs 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 7
241001024304 Mino Species 0.000 description 7
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
125000003282 alkyl amino group Chemical group 0.000 description 7
125000005237 alkyleneamino group Chemical group 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
125000005236 alkanoylamino group Chemical group 0.000 description 6
125000001118 alkylidene group Chemical group 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000013067 intermediate product Substances 0.000 description 6
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
239000011701 zinc Substances 0.000 description 6
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
125000005276 alkyl hydrazino group Chemical group 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
239000011877 solvent mixture Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
125000003396 thiol group Chemical group [H]S* 0.000 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 description 5
125000006016 2-bromoethoxy group Chemical group 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
239000005864 Sulphur Substances 0.000 description 4
229940022663 acetate Drugs 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 4
230000009467 reduction Effects 0.000 description 4
229910052709 silver Inorganic materials 0.000 description 4
239000004332 silver Substances 0.000 description 4
KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
229910021653 sulphate ion Inorganic materials 0.000 description 4
XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 3
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125000001425 triazolyl group Chemical group 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
125000005289 uranyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000344630A 1975-02-20 1980-01-29 Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique Expired CA1140554A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000344630A CA1140554A (fr)	1975-02-20	1980-01-29	Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
CH2157/75		1975-02-20
CH215775A CH626091A5 (en)	1975-02-20	1975-02-20	Process for preparing enol derivatives
CH1096275A CH627759A5 (en)	1975-08-25	1975-08-25	Process for preparing enol ether compounds
CH10962/75		1975-08-25
CA246,040A CA1080695A (fr)	1975-02-20	1976-02-18	Methode de fabrication de derives d'enols
CA000344630A CA1140554A (fr)	1975-02-20	1980-01-29	Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique

Publications (1)

Publication Number	Publication Date
CA1140554A true CA1140554A (fr)	1983-02-01

Family

ID=27425896

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000344630A Expired CA1140554A (fr)	1975-02-20	1980-01-29	Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique

Country Status (1)

Country	Link
CA (1)	CA1140554A (fr)

1980
- 1980-01-29 CA CA000344630A patent/CA1140554A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-02-01	MKEX	Expiry

Publication	Publication Date	Title
CA1059988A (fr)	1979-08-07	Procede pour la fabrication de derives enol
US4293462A (en)	1981-10-06	Process for the manufacture of enol derivatives, and intermediates
CA1060432A (fr)	1979-08-14	DERIVES DE LA 7 .alpha. METOXYCEPHALOSPORINE
CS203927B2 (en)	1981-03-31	Process for preparing 1-oxadethiacephalosporines
US3665003A (en)	1972-05-23	Cephalosporin compounds
US4147864A (en)	1979-04-03	Process for the manufacture of 7β-amino-3-cephem-3-ol-4 carboxylic acid compounds
CA1110231A (fr)	1981-10-06	ACIDES 7-.beta.-AMINO-CEPHAM-3-ONE-4-CARBOXYLIQUES
EP0000645B1 (fr)	1981-01-28	Isopénicillines, procédés pour leur préparation et compositions qui les contiennent
US3835130A (en)	1974-09-10	2-thia-cepham and cephem-4-carboxylic acids
CA1140554A (fr)	1983-02-01	Procede industriel d'obtention de derives de l'acide 2-(2-oxoazetidin-1-yl)-crotonique
EP0000500B1 (fr)	1982-04-28	Dérivés de, cephalosporine leur préparation et leurs compositions pharmaceutiques
US4550162A (en)	1985-10-29	Process for the manufacture of enol derivatives
CH622804A5 (fr)	1981-04-30
US3830808A (en)	1974-08-20	Cephalosporins having a thioetherified methyl group at the 3-position
US4434287A (en)	1984-02-28	Cephalosporin derivatives
US4255328A (en)	1981-03-10	Sulfide intermediates for the manufacture of enol derivatives
US4024249A (en)	1977-05-17	Heteroarylacetamido cephalosporin
US3926957A (en)	1975-12-16	Penicillin antibiotics
US3823140A (en)	1974-07-09	Delta 3-4-carboxy-3-oxobutyl cephalosporins
CA1098512A (fr)	1981-03-31	Procede industriel d'obtention de derives d'enamine
CA1084054A (fr)	1980-08-19	Preparation industrielle de derives de l'acide 3- hydroxy-crotonique
CH615186A5 (en)	1980-01-15	Process for the preparation of cephem compounds
US4579684A (en)	1986-04-01	Process for the manufacture of enol derivatives
US4301278A (en)	1981-11-17	Process for the manufacture of enol derivatives
CA1055924A (fr)	1979-06-05	Composes methoxyheterocycliques a groupes aminomethyle