Trifluoroacetic acid → HCID 178501867, compound

Participants

Reaction Steps

To a suspension of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (11.6 g) and anisole (8.5 g) in dichloromethane (30 ml) was added trifluoroacetic acid (36.5 g) under ice-cooling and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was dropwise added to isopropyl ether (200 ml) under stirring and the precipitates were collected by filtration. The precipitates were dissolved in ethyl acetate and saturated sodium bicarbonate solution and aqueous layer was separated. The aqueous layer was adjusted to pH 4.5 with 10% hydrochloric acid. After removing the solvent in reduced pressure, the solution was acidified to pH 2.5 with 10% hydrochloric acid under ice-cooling. The precipitates were filtered and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (6.1 g).

Provenance & Evidence