Preparation of delta 3-7 alpha-phenylacetamidodesacetoxycephalosporanic acid.

ABSTRACT

delta 3-7 alpha-Phenylacetamidodesacetoxycephalosporanic acid was prepared by ring expansion of 6-epi-benzylpenicillin-S-sulfoxide, using N,O-bis(trimethylsilyl)acetamide (BSA) as silylating and dehydrating agent and alpha-picoline/alpha-picoline hydrobromide as catalyst. In some experiments 7 alpha-phenylacetamido-3 beta-bromo-3 alpha-methylcepham-4 alpha-carboxylic acid was obtained as a side product. 7-Epimers in the desacetoxycephalosporanic series were also prepared by base-catalyzed epimerization of the benzyl 7 beta-(p-nitrobenzylideneimino)desacetoxycephalosporanate and of the S-sulfoxide of natural methyl 6-phenylacetamidodesacetoxycephalosporanate. In both reactions 1,5-diazabicyclo(4.3.0)non-5-ene (DBN) was used as epimerization catalyst.