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

Participants

Reaction Conditions

Reaction Steps

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) was added to 8 mL of methanol. The solution was cooled to −30° C. under the protection of nitrogen flow and then the methanol solution containing 1 mmol of tert-butyl lithium was added. The mixture was stirred at −78° C.˜−20° C. for 2 hours. (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.29 g, 1 mmol) was added and then the mixture was heated slowly to 100° C. and stirred for 2 hours. After the solution was cooled down, 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 evaporated to dryness to provide 0.31 g of white solid in 65% yield. HPLC: 99.2%.

Provenance & Evidence