N-AZAMONOBACTAMS

1. THE SYNTHESIS OF SOME 3-SUBSTITUTED N-AZAMONOBACTAM DERIVATIVES

Abstract

Ring closure of the N-(tert-butyloxycarbonyl)-L-serine 2-(diphenylmethylene)hydrazide (10a) and the corresponding L-threonine derivative (10b) gave good yields of the β-lactams 11a and 11b. Catalytic hydrogenation afforded the corresponding N-ammo β-lactams 12a and 12b. These compounds were then further transformed into 3-(S)-[[(2-amino-4-thiazolyl)-(Z)-(methoxyimino)acetyl]amino-2-oxo-1-azetidinyl]sulfamic acid analogs 18, 23, and 30a and 30b. None of these compounds exhibited any interesting biological activity.