Ammonium Chloride → HCID 10379906, compound

Participants

Reaction Conditions

Reaction Steps

82 ml of a 2.5 molar solution of butyllithium in hexane is added to a solution of 33.06 g (186.6 mmol) of (4S,5R)-4-methyl-5-phenyloxazolidin-2-one in 500 ml of tetrahydrofuran within 30 minutes at −70° C. under argon. Then, a solution of 15.55 ml (187 mmol) of bromoacetyl chloride in 250 ml of tetrahydrofuran is added in drops in such a way that the internal temperature does not exceed −65° C. Then, it is stirred for one more hour at −70° C. Then, the reaction mixture is poured onto 50 ml of saturated aqueous ammonium chloride solution. 90 ml of saturated aqueous sodium bicarbonate solution is then added, allowed to come to 25° C., diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried on sodium sulfate and chromatographed on silica gel. 42.32 g (76%) of the title compound is obtained.

Provenance & Evidence