Monocyclic beta-lactams and process for the preparation thereof

Abstract

Abstract Monocyclic beta -lactam compounds represented by the formula <IMAGE> wherein R1 is H, NH2, acylamino, C1-C4 alkyl, etc.; R2 is e.g. C1-C4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R3 is hydrogen, benzyl, substituted benzyl, pivaloyl, -SO3M, or -P(C=O)(OM')2; are obtained by the cyclization of an O-substituted hydroxamate of a beta -substituted alkylcarboxylic acid. For example, alpha -ethylmalic acid monobenzyl ester is reacted with O-benzylhydroxylamine to form the O-benzylhydroxamate of the free carboxy group, and the hydroxamate is cyclized with diethyl diazodicarboxylate and triphenylphosphine to form the beta -lactam of the above formula wherein R1 is ethyl, R2 is benzyloxycarbonyl and R3 is benzyl. The beta -lactam compounds are useful intermediates for preparing beta -lactamase inhibitors and monocyclic beta -lactam antibiotics and, when R3 is -SO3M or -P(C=O)(OM')2 the compounds and salts thereof are antibacterial agents.

Inventors

• 👤 Marvin J. Miller

Bibliographic Details