1985 Volume 38 Issue 12 Pages 1738-1751
The synthesis and some biological properties of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(carboxymethoxyimino) acetamido]-3-vinyl-3-cephem-4-carboxylic acid (3, FK027)** are described. Diphenylmethyl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (8), the cephem precursor to FK027 was prepared from 7-aminocephalosporanic acid (7-ACA) by two parallel routes differing primarily in the protection of the 7-amino group. Compound 8 was alternatively prepared from deacetylcephalosporin C sodium salt (DCCNa) with improved yields. Two pathways for the conversion of 8 to FK027 are provided. The new orally active cephalosporin, FK027, possesses a widely expanded antimicrobial activity and high stability to β-lactamases.
