反応 #48631

反応方程式

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

収率 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

収率 102.5%

溶媒

N,N-dimethylformamide

ethyl acetate

反応条件

後処理

1. 1
   洗浄wash with water
2. 2
   乾燥dry (magnesium sulfate)
3. 3
   ろ過filter
4. 4
   濃縮concentrate
5. 5
   その他purify
6. 6
   洗浄(silica gel chromatography, eluting with 20:80 to 85:15 ethyl acetate:dichloromethane)

実験手順

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%).

出典