Methanol → HCID 57879596, compound

HRID 1673533Notes

Reaction equation

HRID 1673533 reaction equation
CO.[CH2:3]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:20][C:21](=[O:31])[CH2:22]/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[C].[Pd].C(OCC)(=O)C>[CH2:3]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]=1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 57879390HCID 57879390, compound

Product 1

HCID 57879596HCID 57879596, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.0 mg of 10% palladium-carbon was added to a mixed solution of 0.50 mL of methanol and 0.50 mL ethyl acetate containing 8.0 mg of 4-phenethyl-2-((E)-4-phenyl-3-butenamido)benzoic acid and stirred under hydrogen atmosphere at room temperature for 1 hour and 30 minutes. After insoluble were removed by filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified with silica gel column chromatography [Flash Tube 2003 manufactured by Trikonex Company, eluent; ethyl acetate] to obtain 4.6 mg of 4-phenethyl-2-(4-phenylbutanamido)benzoic acid as white solid.

Workup

  1. customAfter insoluble were removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified with silica gel column chromatography [Flash Tube 2003 manufactured by Trikonex Company, eluent; ethyl acetate]

Sources & evidence

ORD record
ord-d5a25b3642164447bb1f1a421ee64c3c
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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