Ethanol → HCID 66577320, compound

HRID 1512575Notes

Reaction equation

HRID 1512575 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4/[CH:27]=[CH:28]/[C:29]([O:31][CH3:32])=[O:30])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].CCO>[Pd].CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 66578219HCID 66578219, compound

Product 1

HCID 66577320HCID 66577320, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

1-{4′-[4-((E)-2-Methoxycarbonyl-vinyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (1.249 g, 2.89 mmol) and 10% palladium on carbon (0.135 g) were combined in EtOAc (25 mL) and stirred under H2 atmosphere for 4 hours. EtOH (25 mL) was added, along with additional 10% palladium on carbon (one spatula), and the reaction was stirred under H2 for 2 days, replacing the balloon of H2 as needed. When no starting material was seen by analytical LCMS, the mixture was filtered through Celite and the filtrate was concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred under H2 for 2 days
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2b53a828c1db4610b9072a55d36cabd7
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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