Trifluoroacetic acid → HCID 131716132, compound

Participants

Reaction Steps

To a solution of benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(1-ethyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (4.0 g) in dichloromethane (12 ml) were added anisole (4 ml) and trifluoroacetic acid (8 ml) under ice-cooling. After stirring for 4 hours at room temperature, the mixture was poured into diisopropyl ether (250 ml). The resulting precipitate was collected by filtration, washed with diisopropyl ether, and dissolved in 5% sodium bicarbonate solution. The aqueous solution was adjusted to pH 2.5 with 1N hydrochloric acid, andsubjected to column chromatography on non-ionic adsorption resin "HP-20". The desired product was eluted with 5% isopropyl alcohol and the eluate was concentrated and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1-ethyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate (syn isomer) (0.30 g).

Provenance & Evidence