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

HRID 323165

Reaction equation

HRID 323165 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH3:28]C(C)([O-])C.[K+].[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[C:42]([C:47]([NH:49][C:50]3[CH:67]=[CH:66][C:53]([C:54]([N:56]([CH3:65])[C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4C=O)=[O:55])=[CH:52][CH:51]=3)=[O:48])=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:37][CH:36]=1>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[C:42]([C:47]([NH:49][C:50]3[CH:51]=[CH:52][C:53]([C:54]([N:56]([CH3:65])[C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4[CH:28]=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[O:55])=[CH:66][CH:67]=3)=[O:48])=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 220109874-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-formylphenyl)benzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 700687314-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxy-1-pentenyl)phenyl]benzamideYield 67.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To an ice bath cooled solution of (4-carboxybutyl)triphenylphosphonium bromide (371 mg) in N,N-dimethylacetamide (15 ml) was added potassium t-butoxide (188 mg) and the mixture was stirred at the same temperature for 30 minutes. To the resulting mixture was added 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-formylphenyl)benzamide (250 mg) and the mixture was stirred in an ice bath for 3 hours. The mixture was diluted with ethyl acetate (40 ml) and the solution was washed successively with 1N hydrochloric acid (30 ml), water (20 ml) and brine (20 ml). The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The crude oil was purified by silica gel column (1% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypenten-1-yl)phenyl]benzamide (201 mg) as a colorless amorphous.

Workup

  1. stirringthe mixture was stirred in an ice bath for 3 hours
  2. washthe solution was washed successively with 1N hydrochloric acid (30 ml), water (20 ml) and brine (20 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe crude oil was purified by silica gel column (1% methanol in chloroform)

Sources & evidence

ORD record
ord-8da00f1b70e04d54a83cc5747f0c5e8c
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Linked notes

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