Reaktion #1754804

Reaktionsgleichung

((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-benzoimidazole

1-((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-benzoimidazole

(S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid

HOBt

HBTU

diisopropylethylamine

→

{(S)-2-[(S)-2-(2-benzoimidazol-1-yl-pyridin-4-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Ausbeute 67.0%

Lösungsmittel

water

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   WaschenThe combined organic layers are washed with water, sat. NaHCO3, brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated down
6. 6
   SonstigeThe crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 5%˜40%)

Vorschrift

A solution of (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (51 mg, 0.21 mmol), HOBt (31 mg, 0.23 mmol) and HBTU (88 mg, 0.23 mmol) in DMF (5 mL) is stirred at room temperature for 30 min. Then a solution of —((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-benzoimidazole (10) in DMF (5 mL) is added, followed by diisopropylethylamine (135 mg, 1.05 mmol). After stirring at room temperature for 2 h, the reaction mixture is diluted with water and extracted with EtOAc. The combined organic layers are washed with water, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 5%˜40%) to give {(S)-2-[(S)-2-(2-benzoimidazol-1-yl-pyridin-4-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester (71 mg, 67%) as a white solid. M/Z=504.2 [M+1]

Quelle