Trifluoroacetic anhydride → HCID 58964774, compound

Participants

Reaction Steps

A suspension of (R)-N-[4-methylsulphinyl-3-fluoro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 2) (5.41 g) in trifluoroacetic anhydride (65 ml) was heated under reflux for 30 minutes. The reaction mixture was evaporated and the residue was redissolved in MeOH (32 ml) and triethylamine (32 ml) and ethyl iodide (2.2 ml) was added. The reaction mixture was heated under reflux for 3 hours, allowed to cool to room temperature and volatile material was removed by evaporation. The residue was partitioned between EtOAc (150 ml) and brine (100 ml); the organic phase was separated, dried and volatile material was removed by evaporation. The residue was purified by flash column chromatography eluting with 10-20% EtOAc/isohexane to give the title compound (2.16 g) as a yellow solid. NMR (CDCl3) 1.27 (s, 3H), 1.76 (s, 3H), 2.88-2.95 (q, 2H), 3.55 (s, 1H), 7.32 (t, 1H), 8.15 (d, 1H), 8.92 (s, 1H); m/z: 344.

Provenance & Evidence