反応 #48641

反応方程式

triethylamine

(2R,5R)-5-[(1S,2S)-2-amino-3-(3-chloro-5-fluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

acetic anhydride

→

title compound

収率 45.5%

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

収率 45.5%

溶媒

tetrahydrofuran

dichloromethane

反応条件

後処理

1. 1
   洗浄wash with 0.1 N hydrochloric acid (30 mL), saturated aqueous sodium chloride (30 mL)
2. 2
   乾燥dry (sodium sulfate)
3. 3
   ろ過filter
4. 4
   その他purify
5. 5
   洗浄(silica gel chromatography, eluting with 2:98 to 10:90 methanol:dichloromethane)

実験手順

Add triethylamine (138 μL, 0.99 mmol) to a solution of (2R,5R)-5-[(1S,2S)-2-amino-3-(3-chloro-5-fluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.428 g, 0.901 mmol) in tetrahydrofuran (5 mL) followed by acetic anhydride (91 μL, 0.991 mmol). Stir at room temperature for 30 minutes, dilute with dichloromethane, wash with 0.1 N hydrochloric acid (30 mL), saturated aqueous sodium chloride (30 mL), dry (sodium sulfate), filter and purify (silica gel chromatography, eluting with 2:98 to 10:90 methanol:dichloromethane) to give the title compound as a white foam (0.212 g, 45%).

出典