Tetrahydrofuran → 3-[2-(3,3-Dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl ester

HRID 2384166Notes

Reaction equation

HRID 2384166 reaction equation
[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][C:13](C=O)=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:26][CH2:27][CH3:28])=[O:25].[CH2:49]1COCC1>>[CH2:27]([O:26][C:24](=[O:25])[CH:29]=[CH:49][C:13]1[S:12][C:11]([NH:10][C:8]([N:7]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:9])=[N:15][CH:14]=1)[CH3:28]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 578834711,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

Product 1

HCID 767240843-[2-(3,3-Dicyclohexylureido)-thiazol-5-yl]-acrylic acid ethyl esterYield 69%

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f53990d62a3446dd8044835fdaafa117
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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