Hydrochloric Acid → benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-phenylvinylthiomethyl]-3-cephem-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (Z)-2-acetylthiovinylbenzene (500 mg) in tetrahydrofuran (5 ml) was dropwise added a solution of sodium methoxide (13.9 mg) in a mixture of methanol (358 mg) and tetrahydrofuran (2 ml) under ice-cooling. The mixture was stirred for 30 minutes under the same condition. The resulting solution was dropwise added to a solution of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (1.46 g) in tetrahydrofuran (20 ml) at -30° C. The mixture was stirred at the same temperature for 30 minutes. The reaction temperature was gradually raised to 0° C. 1N Hydrochloric acid (3 ml) was added to the reaction mixture at 0° C. Ethyl acetate and a saturated aqueous solution of sodium chloride were added to the mixture. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated in diisopropyl ether to give a solid, which was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of chloroform and methanol (100:1, V/V). The fractions containing the object compound were combined and concentrated in vacuo. The residue was triturated in diisopropyl ether to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-phenylvinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (790 mg).

Provenance & Evidence