CEPHEM COMPOUND, ITS PRODUCTION AND UTILIZATION OF THE COMPOUND FOR PRODUCTION OF CEPHEM ANTIBIOTIC SUBSTANCE

摘要

PURPOSE:To obtain a new cephem compound useful as a production intermediate for cephem antibiotic substance, synthesizable in high yield and, accordingly, capable of producing a cephem antibiotic substance in high yield. CONSTITUTION:This 3-[(E)-1-propenyl]cephem compound is expressed by formula I (R<1> is H, an amino-protecting group, etc.; R<22> is a carboxyl-protecting group; X<1> is H or Cl; R<1> is H and R<22> is not diphenylmethyl when X<1> is H), e.g. p- methoxybenzyl-7beta-[2-phenylacetamido]-3-[(E)-3-chloro-1-propenyl]-3- cephem-4- carboxylate. The compound can be produced by isomerizing a 3-[(Z)-1- propenyl]cephem compound of formula II (R is either one of R<1>; R<2> is a carboxyl-protecting group; X is Hor Cl) in an inert organic solvent in the presence of an aromatic thiol such as thiophenol preferably at 25-110 deg.C.