반응 #48650

반응 방정식

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

수율 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

수율 54.8%

용매

tetrahydrofuran

dichloromethane

반응 조건

후처리

1. 1
   세척wash with 0.1 N hydrochloric acid/saturated aqueous sodium chloride (30 mL)
2. 2
   건조dry (sodium sulfate)
3. 3
   여과filter
4. 4
   농축concentrate
5. 5
   기타purify (silica gel chromatography, eluting with 40:60 to 60:40 ethyl acetate:dichloromethane) acetate/dichloromethane

실험 절차

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%).

출처