Trifluoroacetic acid → HCID 131716067, compound

Participants

Reaction Steps

To a suspension of benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (350 mg) in a mixture of anisol (0.5 ml) and methylene chloride (1.5 ml) was added trifluoroacetic acid (1 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. The mixture was poured into diisopropyl ether (100 ml) and the resulted precipitate was collected. The precipitate was added to a mixture of ice-water and ethyl acetate and adjusted to pH 7 with saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated and adjusted to pH 3 with 6N hydrochloric acid. The precipitate was collected and dried over phosphorus pentoxide to give 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (157 mg).

Provenance & Evidence