HCID 66603896, compound → HCID 66603679, compound

HRID 563672Notes

Reaction equation

HRID 563672 reaction equation
[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[CH2:30][N:31]([CH2:42][CH3:43])[C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C:9]([O:12]CC2C=CC=CC=2)=[CH:10][CH:11]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][C:21]=2[CH2:30][N:31]([CH2:42][CH3:43])[C:32]([NH:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66603896HCID 66603896, compound

Product 1

HCID 66603679HCID 66603679, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

[2′-(3-Benzyl-1-ethyl-ureidomethyl)-6-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (0.580 g, 0.96 mmol) in EtOAc was treated with 10% palladium on carbon (catalytic) and stirred under a balloon of H2 overnight. Analytical tlc indicated that some starting material was still present, so fresh palladium on carbon was added, and the reaction was stirred under a balloon of H2 for an additional 24 hours. Once no starting material was seen by analytical tlc, the mixture was filtered over Celite, and the filtrate was concentrated and purified by silica gel chromatography to give the title compound. M+H is 515.

Workup

  1. stirringthe reaction was stirred under a balloon of H2 for an additional 24 hours
  2. filtrationthe mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f757e7140bc94c19a0481f1121075881
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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