Hydrolysis of 3-cloro-3-cephems. Intramolecular nucleophilic attack in cefaclor

Abstract

The chemical reactivity of 3-chloro-3-cephems was similar to that of the correspondingly substituted 7-aminocephalosporanic acids and 12-13 times greater than that of the correspondingly substituted 7-aminodeacetoxycephalosporanic acids. Cefaclor, 7-(D-2-amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic acid, underwent intramolecular nucleophilic attack at the .beta.-lactam. Loss of Cl from 3-chloro-3-cephem may be a general reaction subsequent to .beta.-lactam opening.