Trifluoroacetic acid → HCID 131714999, compound

Participants

Reaction Steps

Trifluoroacetic acid (6 ml) was added to a solution of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (1.4 g) in methylene chloride (4 ml) and anisole (1.4 ml) under ice-cooling and the mixture was stirred at the same temperature for 40 minutes. The resulting solution was added dropwise to diisopropyl ether (200 ml) and the resultant precipitates were collected by filtration. The precipitates were added to a mixture of water (30 ml) and ethyl acetate (30 ml) and the solution was adjusted to pH 7.0 with 5% aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.7 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylic acid (syn isomer) (0.66 g).

Provenance & Evidence