Reaction #619117

Reaction equation

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

→

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

Yield 47.7%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe content was degassed
2. 2
   FiltrationThe mixture was filtered through celite
3. 3
   Concentrationthe filtrate was concentrated
4. 4
   OtherThe residue was further purified by flash chromatography (silica, CH2Cl2-EtOAc 4:1

Procedure

To a solution of 3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester (Example 257) (75 mg, 0.18 mmol) in methanol was added Pd/C (150 mg). The content was degassed and was placed under hydrogen atmosphere for 12 h. The mixture was filtered through celite, and the filtrate was concentrated. The residue was further purified by flash chromatography (silica, CH2Cl2-EtOAc 4:1 to give 3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-propionic acid ethyl ester (35 mg) in 47% yield.

Source