Réaction #619117

ord-f9113b5512f148d48ddaeec6a083998c

Équation de réaction

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
Rendement 47.7%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE045183E1uspto-grants-2014_10