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filingDate 1994-07-11^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1996-11-26^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_cef850a65eb71ea5859df81f81a15bf1
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_33b20110264064446c0273f97f8cef9d
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publicationDate 1996-11-26^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-5578721-A
titleOfInvention Process for preparation of 3-exomethylene cepham sulfoxide esters
abstract A process for the manufacture of 3-exomethylene cepham sulfoxide ester of the formula ##STR1## wherein R is hydrogen, C 1 -C 3 alkyl, halomethyl, phenyl, substituted phenyl cyanomethyl, phenoxy, benzyloxy or substituted benzyl with a substituent group such as that selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano and trifiuoromethyl, a group of the formula R 2 --0-- wherein R 2 is t-butyl, 2,2,2-trichloro ethyl, benzyl or substituted benzyl; a group of the formula R 3 --[0] n --CH 2 , wherein R 3 is phenyl or substituted phenyl with the substituent group selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano, or 1,4-cyclohexadienyl, and n is 0 or 1; or a substituted arylalkyl group of formula R 4 --CH where R 4 has the same meaning as R 3 defined above and W is a protected hydroxy or protected amino group; and R 1 is a carboxylic acid protecting group such as that selected from the group consisting of C 1 -C 4 alkyl, 2,2,2-trihalo alkyl, benzyl, substituted benzyl such as para nitrobenzyl, phenacyl, halo substituted phenacyl and benzhydryl is disclosed. Such compound is prepared by reacting a chlorosulfinylazetidinone of the formula ##STR2## wherein R and R 1 have the same meanings as defined above, with a Lewis Acid type Friedel-Crafts catalyst and a sulfur compound in an inert solvent under anhydrous condition. These compounds find application as an intermediate for the preparation of cephalosporin antibiotics.
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