Reacción #7444

Ecuación de reacción

Water

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

N,N-dimethylformamide

N,N′-Dicyclohexylcarbodiimide

→

title compound

Rendimiento 51.0%

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

Rendimiento 51.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 20 minutes
2. 2
   Extracciónextracted with ethyl acetate (3×400 ml)
3. 3
   ExtracciónEthyl acetate extract
4. 4
   Lavadowas washed with water (300 ml)
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (6 g, 13.7 mmol) and 2-N-t-butoxy-carbonylamino-4-imidazole propionic acid (5.2 g, 20.3 mmol) in N,N-dimethylformamide (200 ml) was stirred for 1 h at −10° C. N,N′-Dicyclohexylcarbodiimide (4.5 g, 21.8 mmol) was added to this solution and stirring was continued for 12 h at ambient temperature. Water (1800 ml) was added to the reaction mixture, stirred for 20 minutes and extracted with ethyl acetate (3×400 ml). Ethyl acetate extract was washed with water (300 ml), dried over anhydrous sodium sulfate and concentrated to furnish the title compound, which was purified by column chromatography (3.4 g, yield 51%).

Fuente