Triethylamine → Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide

Participants

Reaction Steps

3-Mercapto-6-methylpyridazine (1 g) was added to a mixture of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (5.0 g) in N,N-dimethylformamide (25 ml) and triethylamine (0.7 g) under ice-cooling and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (4.8 g).

Provenance & Evidence