Ammonium Chloride → (S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

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N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) and lithium tert-butoxide (0.10 g, 1.3 mmol) were added under nitrogen atmosphere to 10 mL of tetrahydrofuran and the mixture was stirred at room temperature for 2 hours (Solution 1). (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.32 g, 1.1 mmol) and lithium tert-butoxide were added to 10 mL tetrahydrofuran and stirred at room temperature for 2 hours (Solution 2). Solution 2 was added to Solution 1 and the material liquid was heated to 50° C. and reacted for 5 hours. Saturated ammonium chloride solution, and ethyl acetate were added to separate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 0.40 g of off-white solid in 84% yield.

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