Sodium Iodide → 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

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Reaction Steps

6-Mercapto-1,2,4-triazolo[4,3-b]pyridazine (4.7 g) was added to a stirred suspension of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (5.0 g) and sodium iodide (4.6 g) in N,N-dimethylformamide (35 ml) and the mixture was stirred for 2 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate and water and then the resultant mixture was adjusted to pH 7.5 with 20% aqueous solution of sodium carbonate. The separated organic layer was washed with saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The crude product obtained by concentration of organic layer was purified by silica gel column chromatography using ethyl acetate as an eluate. The fractions containing the object compound were 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 (syn isomer) (1.2 g).

Provenance & Evidence