Ammonium Chloride → (4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one

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Reaction Steps

To a tetrahydrofuran (300 ml) solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (26.58 g), 1.58 M of n-butyl lithium (tetrahydrofuran solution; 100 ml) was added under argon atmosphere at −78° C., and the mixture was stirred at the same temperature for 40 minutes. To the mixture, a tetrahydrofuran (100 ml) solution of 5-phenylpentanoyl chloride (32.4 g) was added, followed by stirring at −78° C. for 5 minutes. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively, dried over anhydrous sodium sulfate and concentrated to give the title compound (55.29 g) having the following physical properties.

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