反応 #48650

反応方程式

5-(R)-(2-(S)-amino-1-(S)-hydroxy-3-phenylpropyl)-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

triethylamine

acetic anhydride

→

title compound

収率 54.8%

5-(R)-(2-(S)-Acetylamino-1-(S)-hydroxy-3-phenyl-propyl)-2-(S)-(2-cyclohexyl-ethyl)-morpholine-4-carboxylic acid tert-butyl ester

収率 54.8%

溶媒

tetrahydrofuran

dichloromethane

反応条件

後処理

1. 1
   洗浄wash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL)
2. 2
   乾燥dry (sodium sulfate)
3. 3
   ろ過filter
4. 4
   濃縮concentrate
5. 5
   その他purify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane

実験手順

Dissolve 5-(R)-(2-(S)-amino-1-(S)-hydroxy-3-phenylpropyl)-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester (140 mg, 0.31 mmol) in dry tetrahydrofuran (3 mL). Add triethylamine (0.05 mL, 0.35 mmol) followed by acetic anhydride (0.03 mL, 0.35 mmol) and stir at room temperature for 1 hour. Dilute with dichloromethane, wash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL), dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane to give the title compound (83 mg, 54%).

出典