Methanol → HCID 57879469, compound

HRID 1673423Notes

Reaction equation

HRID 1673423 reaction equation
CO.[C:3]([NH:11][C:12]1[CH:20]=[C:19](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[C].[Pd].C(OCC)(=O)C>[C:3]([NH:11][C:12]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 57879495HCID 57879495, compound

Product 1

HCID 57879469HCID 57879469, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9 mg of 5% palladium-carbon was added to a mixed solution of 2.7 mL of methanol and 2.7 mL of ethyl acetate containing 30 mg of 2-benzamido-4-((E)-2-(3-chlorophenyl)vinyl)benzoic acid and stirred under hydrogen atmosphere at room temperature for 3 hours. Insoluble were removed by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 2.0 mg of 2-(benzamido)-4-(2-(3-chlorophenyl)ethyl)benzoic acid as white solid.

Workup

  1. customInsoluble were removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-6a73432524c1482397776d1f6c478f79
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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