Reaction #340984

Reaction equation

1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

(carbethoxymethylene)triphenylphosphorane

THF

→

3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester

Yield 69.0%

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   Otherthe residue was purified by flash chromatography (silica, CH2Cl2-EtOAc, 4:1)

Procedure

A solution of 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (Example 252) (90 mg, 0.27 mmol) and (carbethoxymethylene)triphenylphosphorane (102 mg, 0.30 mmol) in THF (5 mL) was stirred at 40° C. for 12 h. The reaction mixture was concentrated and the residue was purified by flash chromatography (silica, CH2Cl2-EtOAc, 4:1) to obtain 3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester (75 mg) in 69% yield.

Source