Reaktion #1938639

Reaktionsgleichung

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride

7-(benzyloxy)-1H-indole-2-carboxylic acid

2-(tritylthio)ethylamine hydrochloride

1H-1,2,3-benzotriazol-1-ol

→

title compound

Ausbeute 94.0%

7-(Benzyloxy)-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Ausbeute 94.0%

Lösungsmittel

N,N-dimethylformamide

triethylamine

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe ethyl acetate layer was washed with saturated brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated

Vorschrift

To a mixture of 7-(benzyloxy)-1H-indole-2-carboxylic acid (0.80 g), 2-(tritylthio)ethylamine hydrochloride (1.07 g), 1H-1,2,3-benzotriazol-1-ol (0.49 g), triethylamine (0.50 mL) and N,N-dimethylformamide (15 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.69 g) at 0° C., and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (1.60 g, yield 94%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 156-157° C.

Quelle