(4-Fluoro-3-phenoxyphenyl)methanol → N-(p-chlorophenyl)valine

Participants

Reaction Steps

To a solution of 3-(4-chlorophenyl)-4-isopropyloxazolidine-2, 5-dione (336 mg, 1.32 mmol) and 4-dimethylaminopyridine in 5 ml of dry tetrahydrofuran is added a solution of 4-fluoro3-phenoxybenzyl alcohol (275 mg, 1.26 mmol) in 3 ml of dry tetrahydrofuran. The reaction mixture is stirred for about 20 hours, under dry air, and then diluted with ether followed by washing with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride. After drying over calcium sulfate, solvent is evaporated. The crude product, yellow liquid, is chromatographed on a rotary chromatograph eluting with 15% ether/hexane to give the 4-fluoro-3-phenoxybenzyl ester of N-(4-chlorophenyl) valine.

Provenance & Evidence