Reaktion #619117

ord-f9113b5512f148d48ddaeec6a083998c

Reaktionsgleichung

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
Ausbeute 47.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10