Trifluoromethanesulfonic anhydride → HCID 86598333, compound

Participants

Reaction Steps

Trifluoromethanesulfonic anhydride (1.51 ml) was added dropwise to an ice-cold solution of N-trifluoroacetyl-3-hydroxy-L-phenylalanine ethyl ester (915 mg, 3.00 mmol) in pyridine (9 ml) in 5 minutes under argon atmosphere. The mixture was stirred at the same temperature for 30 minutes and then at room temperature for 16 hrs. The reaction mixture was poured into ice-water (500 ml) and extracted with ethyl acetate. The extract was washed with 10% hydrochloric acid, water and brine in turn and then dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7) to give N-trifluoroacetyl-3-trifluoromethanesulfonyloxy-L-phenylalanine ethyl ester (1.25 g, 95%) as pale yellow crystals.

Provenance & Evidence