반응 #48723

반응 방정식

1-bromo-2-methyl-propane

(2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

cesium carbonate

→

title compound

수율 55.0%

(2R,3S,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-fluoro-5-isobutoxy-phenyl)-1-hydroxypropyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

수율 55.0%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   온도Cool to room temperature
2. 2
   세척Wash (0.1N citric acid, 10% potassium carbonate, saturated aqueous sodium chloride)
3. 3
   건조dry (magnesium sulfate)
4. 4
   여과filter
5. 5
   농축concentrate
6. 6
   기타Purify on 12 g silica gel column
7. 7
   세척eluting with 100:0 to 40:60 hexanes

실험 절차

Add 1-bromo-2-methyl-propane (0.05 g, 0.35 mmol) to (2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (0.12 g, 0.23 mmol) and cesium carbonate (0.15 g, 0.46 mmol) in N,N-dimethylformamide (3 mL) under nitrogen and heat in a 60° C. oil bath for 2.5 hours. Cool to room temperature and dilute with ethyl acetate. Wash (0.1N citric acid, 10% potassium carbonate, saturated aqueous sodium chloride), dry (magnesium sulfate), filter and concentrate. Purify on 12 g silica gel column eluting with 100:0 to 40:60 hexanes:ethyl acetate to give 0.072 g (54.5%) of the title compound as a white foam.

출처