Penicillin C-6 substitution using the versatile 6α-succinimido-oxy leaving group
Abstract
Reaction of benzyl 6α-(methylthio)-6β-(phenoxyacetamido)penicillanate with N-hydroxysuccinimide catalysed by silver(I) acetate afforded the stable 6α-(succinimido-oxy) dervative; this species on reaction with various nucleophiles gave a range of 6α-substituted penicillins, including some not directly available from the 6α-(methylthio) compound.