http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1315995-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_fdaa64756184e715af6cb25ebc318917 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D205-09 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D205-095 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D205-095 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D205-09 |
| filingDate | 1970-07-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1973-05-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1315995-A |
| titleOfInvention | Substituted azetidinones |
| abstract | 1315995 Azetidinone derivatives YEDA RESEARCH & DEVELOPMENT CO Ltd 22 June 1971 [31 July 1970] 37057/70 Heading C2C Azetidin-2-ones having a thioether substituent in the 4-position and a halogen, azido or dicarboxylic acid imido group in the 3-position, and especially novel compounds of formula where X is halogen, azido or dicarboxylic acid imido, R is optionally substituted alkyl or aralkyl, R<SP>1</SP> is optionally substituted alkoxy or aralkoxy, R<SP>2</SP> and R<SP>3</SP> are H or optionally substituted alkyl, aralkoxy or alkylthioalkyl, and Y and Z are each H or together represent a bond joining the carbons to which they are attached, are prepared by reacting a thioimidate derivative of an α-amino acid with XCHCOHal under anhydrous conditions in the presence of a tertiary base. X=Cl may subsequently be converted to X=azido by means of NaN 3 . Compounds of formula where R<SP>4</SP> is -CH(CH 3 ) 2 , -CH 2 OCH 2 C 6 H 5 , -CH 2 CH 2 SCH 3 and -C(CH 3 ) 2 SCH 3 are prepared by reacting appropriate amino acid esters with HCSOC 2 H 5 . is obtained from HC(NH)OC 2 H 5 and the corresponding amino acid ester. Starting materials of formula where: R<SP>5</SP>=CH 3 , R<SP>4</SP>=-CH(CH 3 ) 2 ; R<SP>5</SP>= C 6 H 5 CH 2 -, R<SP>4</SP> =-CH(CH 3 ) 2 ; R<SP>5</SP> = CH 3 , R<SP>4</SP>=-CH 2 OCH 2 C 6 H 5 ; R<SP>5</SP> = CH 3 , R<SP>4</SP>= -CH 2 CH 2 SCH 3 ; R<SP>5</SP>=4-NO 2 -C 6 H 4 CH 2 -, R<SP>4</SP>=-CH 2 CH 2 SCH 3 ; and R<SP>5</SP>=CH 3 , R<SP>4</SP> = -C(CH 3 ) 2 SCH 3 are prepared by reacting R<SP>5</SP>Hal with HC(S)NHCHR<SP>4</SP>COOCH 3 ; where R<SP>5</SP>= CH 3 OOCCH 2 CH 2 - and R<SP>4</SP>=-CH(CH 3 ) 2 and -CH 2 OCH 2 C 6 H 5 by reacting with the compounds in which R<SP>5</SP> = CH 3 or with C 2 H 5 OCH = NCH(COOCH 3 )CH(CH 3 ) 2 . CH 3 SCH = NC(COOCH 3 ) = C(CH 3 ) 2 is prepared from and CH 3 I in the presence of NaH. Phthaloylglycylvaline methyl ester is obtained as a by-product of the reaction between phthaloylglycylchloride and when R<SP>5</SP> is CH 3 - or C 6 H 5 CH 2 -. |
| priorityDate | 1970-07-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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