4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxy-1-pentenyl)phenyl]benzamide → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypentyl)phenyl]benzamide

HRID 323144Notes

Reaction equation

HRID 323144 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:40]=[CH:39][C:20]([C:21]([N:23]([CH3:38])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH:30]=[CH:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:38])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:22])=[CH:39][CH:40]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 700687314-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxy-1-pentenyl)phenyl]benzamide

Product 1

HCID 220109464-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypentyl)phenyl]benzamideYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxy-1-pentenyl)phenyl]benzamide (150 mg) in ethanol (10 ml) was shaken under hydrogen atmosphere (3 atm.) in the presence of 10% palladium on carbon (50 mg) for 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo and the residue was subjected to silica gel column (29% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypentyl)phenyl]benzamide (150 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9698f96468db4fa085f2718ccce729df
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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