Reacción #7449

Ecuación de reacción

Water

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

2-t-butoxycarbonylamino propionic acid

N,N′-Dicyclohexylcarbodiimide

→

crude compound

Rendimiento 36.3%

5-[4-(4-(2-(2-t-Butoxycarbonylaminopropanamido)-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione

Rendimiento 36.3%

Disolventes

dimethyl formamide

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 15 minutes
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for another 15 minutes
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with water (100 ml)
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Concentraciónconcentrated

Procedimiento

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (2 g, 4.6 mmol) and 2-t-butoxycarbonylamino propionic acid (0.87 g, 4.6 mmol) in dimethyl formamide (10 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (1.139 g, 5.5 mmol) was added to this solution and stirring was continued for 2 h at ambient temperature. Water (200 ml) was added to the reaction mixture, stirred for 15 minutes, ethyl acetate (250 ml) added and stirring was continued for another 15 minutes. The organic layer was separated and washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated to furnish the crude compound which was purified by column chromatography (0.95 g, yield 36.3%).

Fuente