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

HRID 2384167Notes

Reaction equation

HRID 2384167 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]=[CH:6][C:7]1[S:11][C:10]([NH:12][C:13]([N:15]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])=[N:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[S:11][C:10]([NH:12][C:13]([N:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:14])=[N:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 578837633-[2-(3,3-Dicyclohexylureido)-thiazol-5-yl]-propionic acid ethyl esterYield 47.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-58cc90e1c8a54eafa5244764b1136a52
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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