反応 #48630

反応方程式

acetic anhydride

N,N-diisopropylethylamine

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

→

desired compound

収率 34.7%

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

収率 34.7%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   洗浄wash with 1 N hydrochloric acid (twice), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
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 25:75 ethyl acetate:hexanes)

実験手順

Add acetic anhydride (320 μL, 3.4 mmol) and N,N-diisopropylethylamine (590 μL, 3.4 mmol) to a solution of 5-(R)-[2-(S)-amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester (770 mg, 1.70 mmol). Stir for 2.5 hours. Dilute with ethyl acetate, wash with 1 N hydrochloric acid (twice), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 20:80 to 25:75 ethyl acetate:hexanes) to give the desired compound (292 mg).

出典