Reaktion #48641

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 45.5%

Lösungsmittel

tetrahydrofuran

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwash with 0.1 N hydrochloric acid (30 mL), saturated aqueous sodium chloride (30 mL)
2. 2
   Trocknendry (sodium sulfate)
3. 3
   Filtrationfilter
4. 4
   Sonstigepurify
5. 5
   Waschen(silica gel chromatography, eluting with 2:98 to 10:90 methanol:dichloromethane)

Vorschrift

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%).

Quelle