Dimethylformamide → 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzamide

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Reaction Steps

A stirred, ice-cooled, DMF (60 mL) solution of the 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid (8.5 g, ˜80%, 23.6 mmol) triethylamine (6.6 mL, 47.2 mmol) was added and after 2-3 minutes TBTU (8.3 g, 26 mmol) was added. After stirring for 30 minutes, ammonium hydroxide solution (7 mL, 98 mmol) was added and stirred for 40 minutes. The reaction mixture was diluted with 500 mL of saturated aqueous sodium bicarbonate solution and extracted with three 200 mL portions of dichloromethane. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzamide as a colorless thick oil which solidified on standing (6.0 g, 90%).

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