Conversion of benzyl 6-diazopenicillanate into 6-phenylacetylhydrazono- and 6β-phenylacetylhydrazino-penicillanic acid

Abstract

Benzyl 6-diazopenicillanate (1; R¹= N₂, R²= CH₂Ph) has been converted into 6-acetyl- and 6-phenylacetyl-hydrazonopenicillanic acid (3; R¹= Me, R²= H and R¹= PhCH₂, R²= H) and 6β-acetyl- and 6β-phenylacetyl-hydrazinopenicillanic acid (4; R¹= Me, R²= H and R¹= PhCH₂, R²= H); the latter is an effective antibiotic against a penicillin-resistant strain of Staphalococcus aureus.