Trifluoroacetic acid → HCID 70262478, compound

Participants

Reaction Steps

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-[2-(3-pyridyl)ethylthio]-3-cephem-4-carboxylate (632 mg) in a mixture of dichloromethane (1.8 ml) and anisole (0.6 ml) was added trifluoroacetic acid (1.2 ml) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hours. The reaction mixture was poured into diisopropyl ether (60 ml), and the resulting precipitate was collected by filtration and dried in vacuo. The precipitate was dissolved in a mixture of aqueous sodium hydrogen carbonate (188 mg/50 ml), tetrahydrofuran (20 ml) and ethyl acetate (40 ml). To the separated aqueous layer was added tetrahydrofuran (20 ml) and ethyl acetate (40 ml), adjusted to pH 3.0 with 1N-hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, ethyl acetate and n-hexane, and dried to give 7β-(2-phenylacetamido)-3-[2-(3-pyridyl)ethylthio]-3-cephem-4-carboxylic acid (366 mg).

Provenance & Evidence