반응 #48612

반응 방정식

(R)-4-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

triethylamine

acetic anhydride

→

desired compound

수율 72.4%

(R)-4-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

수율 72.4%

용매

tetrahydrofuran

ethyl acetate

반응 조건

후처리

1. 1
   세척wash with water (twice), 0.1 N hydrochloric acid, and saturated aqueous sodium chloride
2. 2
   건조Dry (magnesium sulfate)
3. 3
   여과filter
4. 4
   농축concentrate
5. 5
   기타purify (silica gel chromatography 0:100 to 70:30 ethyl acetate:hexanes)

실험 절차

Dissolve (R)-4-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (920 mg, 2.38 mmol) in dry tetrahydrofuran (20 ml) under an atmosphere of nitrogen. Add to the resulting solution triethylamine (400 μl, 2.87 mmol) and acetic anhydride (235 μL, 2.49 mmol). After 1 hour, dilute with ethyl acetate and wash with water (twice), 0.1 N hydrochloric acid, and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography 0:100 to 70:30 ethyl acetate:hexanes) to give the desired compound as a white solid (738 mg, 72% yield).

출처