Réaction #7444

Équation de réaction

Water

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

N,N-dimethylformamide

N,N′-Dicyclohexylcarbodiimide

→

title compound

Rendement 51.0%

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

Rendement 51.0%

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 20 minutes
2. 2
   Extractionextracted with ethyl acetate (3×400 ml)
3. 3
   ExtractionEthyl acetate extract
4. 4
   Lavagewas washed with water (300 ml)
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated

Mode opératoire

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%).

Source