m-Chloroperbenzoic acid → Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide

Participants

Reaction Steps

A solution of m-chloroperbenzoic acid (0.4 g) (purity: 80%) in ethyl acetate (5 ml) was added to a solution of a mixture (1.4 g) of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) and benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-2-cephem-4-carboxylate (syn isomer) in ethyl acetate (10 ml) under ice-cooling and the resultant mixture was stirred for 1 hour at the same temperature. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively. The organic layer was dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (1.3 g).

Provenance & Evidence