Reaktion #340984

ord-034e7e50669d4473b1b44b642411f934

Reaktionsgleichung

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
(carbethoxymethylene)triphenylphosphorane
C1CCOC1
THF
CCOC(=O)C=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
3-[2-(3,3-dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester
Ausbeute 69.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07872139B2uspto-grants-2011_01