Reacción #437930

Ecuación de reacción

3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propionic acid

diethyl cyanophosphate

thiomorpholine-1,1-dioxide hydrochloride

triethylamine

→

4-{3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl}thiomorpholine-1,1-dioxide

Disolventes

N,N-dimethylformamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   Lavadowashed with 0.1N aqueous sodium hydroxide solution and water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   FiltraciónThe precipitated solid was collected by filtration

Procedimiento

A mixture of 3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propionic acid (2.67 g), diethyl cyanophosphate (1.69 g), thiomorpholine-1,1-dioxide hydrochloride (1.62 g), triethylamine (2.9 ml) and N,N-dimethylformamide (40 ml) was stirred at room temperature for 3 hrs. The reaction mixture as poured into water, extracted with ethyl acetate, washed with 0.1N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate and concentrated. The precipitated solid was collected by filtration to give 4-{3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl}thiomorpholine-1,1-dioxide as a colorless powder. Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 220–222° C.

Fuente