Réaction #7443

Équation de réaction

Diethylamine

N,N′-dicyclohexylcarbodiimide

5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride

hydroxylbenzotriazole

→

title compound

Rendement 163.8%

5-[4-(4-(2-(2-amino-3-imidazol-4-ylpropanamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione dihydrochloride

Rendement 163.8%

Solvants

N,N-dimethyl formamide

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated in vacuum
2. 2
   LavageThe obtained residue was washed with 10% sodium bicarbonate, brine
3. 3
   Autrepurified with preparative HPLC

Mode opératoire

Diethylamine (1.04 ml, 6.0 mmol) and N,N′-dicyclohexylcarbodiimide (0.64 g, 3.13 mmol) were added to the stirred suspension of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (1.3 g, 3.0 mmol), 2-N-t-butoxycarbonylamino-4-imidazole propionic acid (0.8 g, 3.13 mmol) and hydroxylbenzotriazole (0.42 g, 3.13 mmol) in N,N-dimethyl formamide (15 ml). The stirring was continued for 24 h and the reaction mixture was concentrated in vacuum. The obtained residue was washed with 10% sodium bicarbonate, brine and purified with preparative HPLC to yield the title compound (1.5 g, yield 79%).

Source