Reaktion #40705

Reaktionsgleichung

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

Ausbeute 37.3%

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

Ausbeute 37.3%

Lösungsmittel

Et3N

Et3N

dichloromethane

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 0-4° C. for 1 hour
2. 2
   Sonstigeat room temperature
3. 3
   Sonstigeovernight
4. 4
   Sonstigethe organic phase was separated off
5. 5
   SonstigeDrying
6. 6
   Sonstigeevaporating the solvent

Vorschrift

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.

Quelle