Carbon and oxygen analogs of cephalosporins

Details Carbon and oxygen analogs of cephalosporins Carbon and oxygen analogs of cephalosporins

C - Chemistry, Metallurgy

07

D

260/102, 260/108

C07D 501/00 (2006.01) C07D 499/00 (2006.01)

Patent

CA 1102308

Abstract of the Invention In accordance with this invention, it has been found that biologically active 7-carbon and 7-oxygen analogs of cephalosporins and derivatives thereof can be formed from corres- ponding 6-carbon and 6-oxygen analogs of penicillins by re- arrangement. Such re-arrangement is effected through the inter- mediacy of an .alpha.-or .beta.-sulfoxide of esters of 6-carbon and 6-oxygen analogs of penicillins. This intermediate sulfoxide, prepared by oxidation of an ester of a 6-carbon or 6-oxygen analog of 6-acylamido penicillanic acid; is transformed into the desired 7-carbon and 7-oxygen analogs of 7-acylamido cephalosporanic acid by heating in the presence of a trace of acid and subsequent removal of the protective ester group.

261186

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