Water → tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]carbamate

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 39 mg, 0.975 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (202 mg, 0.567 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (141 μL, 1.131 mmol) in N,N-dimethylformamide at −25° C. After 15 min, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (2×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (0% hexanes→30% ethyl acetate/hexanes) gave the title compound (105 mg). MS 439.1 (M+1).

Provenance & Evidence