{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl ester → {3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid

HRID 2114181Notes

Reaction equation

HRID 2114181 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:22]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:20])=[C:14]([C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[CH:13]=1)C1C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH3:39][N:38]([CH3:40])[C:37]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[NH:18][C:19]([C:21]1[C:22]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=2)=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20])[O:11][CH2:10][C:9]([OH:42])=[O:8])=[O:41]

Participants

4

Reactant 1

HCID 58706373{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl ester

Product 1

HCID 23130252{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acidYield 53.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

{3-Dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl ester (260 mg) was dissolved in ethyl acetate (5 mL), and thereto was added 7.5% palladium carbon (250 mg). The mixture was stirred for 1 hour under hydrogen atomosphere. The reaction solution was filtered through a Celite and the filtrate was concentrated to give {3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid (118 mg).

Workup

  1. filtrationThe reaction solution was filtered through a Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-15ab6cd254784ab8881774f538a75c05
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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