تفاعل #48641

معادلة التفاعل

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

المردود 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

المردود 45.5%

المذيبات

tetrahydrofuran

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   غسيلwash with 0.1 N hydrochloric acid (30 mL), saturated aqueous sodium chloride (30 mL)
2. 2
   تجفيفdry (sodium sulfate)
3. 3
   ترشيحfilter
4. 4
   أخرىpurify
5. 5
   غسيل(silica gel chromatography, eluting with 2:98 to 10:90 methanol:dichloromethane)

الإجراء التجريبي

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%).

المصدر