Methanol → (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylic acid

HRID 1515035Notes

Reaction equation

HRID 1515035 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[N:21]=[C:20]([C:22]4[C:27]([CH3:28])=[CH:26][C:25](/[CH:29]=[CH:30]/[C:31]([O:33]C)=[O:32])=[CH:24][C:23]=4[CH3:35])[NH:19][C:18]=3[CH:36]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO>O.CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[N:21]=[C:20]([C:22]4[C:23]([CH3:35])=[CH:24][C:25](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])=[CH:26][C:27]=4[CH3:28])[NH:19][C:18]=3[CH:36]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66965696methyl (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylate

Product 1

HCID 66965979(E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of methyl (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylate (200 mg, 420 μmol), 1N NaOH (520 μL), and methanol (260 μL) was diluted with 3 mL of water/methanol (2:1) and stirred at ambient temperature for 18 h. The solution was then quenched with 1N HCl (520 μL), filtered, and the precipitate washed with water and dried, to yield (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylic acid. 1H-NMR (DMSO-d6, 400 MHz): δ 8.31 (s, broad, 1H), 7.87 (d, J=8.3 Hz, 1H), 7.74 (d, J=8.7 Hz, 2H), 7.67 (m, 1H), 7.58 (m, 3H), 7.37 (d, J=8.7 Hz, 2H), 6.63 (d, J=16.2 Hz, 1H), 2.15 (s, 6H), 1.29 (s, 9H). MS (ESI) m/z 468.2 (M+H): Retention time=1.24 min (Method 10).

Workup

  1. customThe solution was then quenched with 1N HCl (520 μL)
  2. filtrationfiltered
  3. washthe precipitate washed with water
  4. customdried

Sources & evidence

ORD record
ord-9ac6fc1c0b1d4774b04c39c88205a160
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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