Reacción #40705

Ecuación de reacción

3-amino-2-hydroxy-4-phenylbutanamide hydrochloride

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

hydroxylbenzotriazole

2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acid

NaHCO3

→

reddish oil

Rendimiento 37.3%

N-[3-Amino-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxamide

Rendimiento 37.3%

Disolventes

Et3N

Et3N

dichloromethane

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at 0-4° C. for 1 hour
2. 2
   Otroat room temperature
3. 3
   Otroovernight
4. 4
   Otrothe organic phase was separated off
5. 5
   OtroDrying
6. 6
   Otroevaporating the solvent

Procedimiento

0.75 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 0.51 g of hydroxylbenzotriazole (HOBt) and 0.55 ml of triethylamine (Et3N) were successively added to a solution of 1.0 g of 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acid (3.77 mmol) in 50 ml of dichloromethane at 0-4° C., and the mixture was stirred at 0-4° C. for 1 hour. 0.9 g of 3-amino-2-hydroxy-4-phenylbutanamide hydrochloride (3.9 mmol) and 0.55 ml of Et3N were then added and, after about 5 minutes, a pH of 8-9 was adjusted by adding 0.5 ml of Et3N. The mixture was stirred at 0-4° C. for 1 hour and then at room temperature overnight. 50 ml of saturated NaHCO3 solution were then added to the mixture, and the organic phase was separated off. Drying and evaporating the solvent resulted in 620 mg of a reddish oil, which was reacted further immediately without further purification.

Fuente