Réaction #40705

Équation de réaction

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

Rendement 37.3%

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

Rendement 37.3%

Solvants

Et3N

Et3N

dichloromethane

triethylamine

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at 0-4° C. for 1 hour
2. 2
   Autreat room temperature
3. 3
   Autreovernight
4. 4
   Autrethe organic phase was separated off
5. 5
   AutreDrying
6. 6
   Autreevaporating the solvent

Mode opératoire

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.

Source