반응 #48631

반응 방정식

1-bromobutane

5-[2-(S)-acetylamino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester

cesium carbonate

→

title compound

수율 102.5%

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

수율 102.5%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   세척wash with water
2. 2
   건조dry (magnesium sulfate)
3. 3
   여과filter
4. 4
   농축concentrate
5. 5
   기타purify
6. 6
   세척(silica gel chromatography, eluting with 20:80 to 85:15 ethyl acetate:dichloromethane)

실험 절차

Add 1-bromobutane (6 μL, 55.6 μmol) to a solution of 5-[2-(S)-acetylamino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester (25 mg, 50.5 μmol) and cesium carbonate (33 mg, 1.01 mmol) in N,N-dimethylformamide (250 μL). Heat to 60° C. for 3 hours. Dilute with ethyl acetate, wash with water, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 20:80 to 85:15 ethyl acetate:dichloromethane) to give the title compound (28.5 mg, 80%).

출처