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 253803Notes

Reaction equation

HRID 253803 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-11492f36587a479c9c2aa9513692b197
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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