Reacción #619117

ord-f9113b5512f148d48ddaeec6a083998c

Ecuación de reacción

CCOC(=O)C=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester
CCOC(=O)CCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-propionic acid ethyl ester
Rendimiento 47.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045183E1uspto-grants-2014_10