Реакция #48650

Уравнение реакции

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

Выход 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

Выход 54.8%

Растворители

tetrahydrofuran

dichloromethane

Условия реакции

Обработка

1. 1
   Промывкаwash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL)
2. 2
   Сушкаdry (sodium sulfate)
3. 3
   Фильтрацияfilter
4. 4
   Концентрированиеconcentrate
5. 5
   Другоеpurify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane

Методика

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%).

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