Reaktion #48760

Reaktionsgleichung

cyclopentanecarboxylic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

1-hydroxybenzotriazole monohydrate

(2R,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

triethylamine

→

desired compound

Ausbeute 98.3%

(2R,5R)-5-[(1S,2S)-2-(Cyclopentanecarbonylamino)-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

Ausbeute 98.3%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenWash with saturated aqueous sodium bicarbonate
2. 2
   Trocknendry (magnesium sulfate)
3. 3
   Filtrationfilter
4. 4
   Einengenconcentrate
5. 5
   Sonstigepurify
6. 6
   Waschen(silica gel chromatography, eluting with 80:20 hexane:ethyl acetate)

Vorschrift

Stir cyclopentanecarboxylic acid (0.01 mL, 0.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.02 g, 0.12 mmol) and 1-hydroxybenzotriazole monohydrate (HOBT) (0.02 g, 0.12 mmol) in dichloromethane (1 mL) at room temperature for 30 minutes. Add (2R,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.05 g, 0.11 mmol) in dichloromethane (1 mL) and triethylamine (0.06 mL, 0.44 mmol) and stir at room temperature overnight. Wash with saturated aqueous sodium bicarbonate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 80:20 hexane:ethyl acetate), to give the desired compound as white solid (0.06 g, 98%).

Quelle