Process for the preparation of N - acyl - benzyl - penicillins and N - acyl - benzyl - penicillins obtained correlated

摘要

Title cpds. are of formula I:- and salts and esters of I, where R is alpha-amino-benzyl, alpha-carboxylbenzyl, 2- or 3-thienylmethyl, 2- or 3-thienylaminomethyl, alpha-amino-p-hydroxybenzyl, or R2R3R'4C-, where R1 = Ph opt. substd. by 2-Cl or 2,6-dichloro; R2 = aryl, alpha- or beta-thienyl, o -, m-, or p - oxyaryl, or O-aryl or S - aryl opt. subst. by hal; R3 = H, (1-10C) alkyl, (1-10C)O -aryl, NH2, (1-6C) NH alkyl, (2-6C)N(alkyl)2, CO2H, (2-8C)CO2 alkyl, carbomethylacyloxy, or carboxybenzyl; and R4 = H; or R2CR3 tog. form a (5-7C)cycloaliphatic ring and R4 =NH2, (1-6C)NH alkyl or (2-6C)N(alkyl)2. I are prepd. from C -protected benzyl penicillins by (a) N - metallation e.g. with NaH or Li Bu, (b) reaction with an acyl halide RCOX and (c) removal of the C - protecting residue.