Hydrochloric Acid → 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid

HRID 1515033Notes

Reaction equation

HRID 1515033 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22](=[O:34])[NH:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1.[OH-].[Na+].Cl>CO>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:22]([C:19]2[CH:20]=[CH:21][C:15]3[N:14]=[C:13]([C:9]4[C:8]([CH3:35])=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:11][C:10]=4[CH3:12])[NH:17][C:16]=3[CH:18]=2)=[O:34])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669656413-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

Product 1

HCID 601505823-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester (310 mg, 640 mmols) and 3.2 mL of 1N sodium hydroxide in MeOH (1.6 mL) was stirred until the reaction was complete. The solution was neutralized to pH 4-5 with 1N hydrochloric acid and the resulting precipitate was filtered, washed with water, and dried under reduced pressure to afford 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid. 1H-NMR (DMSO-d6, 400 MHz): δ 12.17 (s, broad, 1H), 10.22 (s, 1H), 8.29 (s, broad, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 7.72 (m, 1H), 7.37 (d, J=9.0 Hz, 2H), 7.10 (s, 2H), 2.85 (t, J=7.3 Hz, 2H,), 2.59 (t, =7.3 Hz, 2H), 2.10 (s, 6H). MS (ESI) m/z 470.2 (M+H). High resolution MS (M+H): theory 470.2444, measured 470.2434.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-76d9b4e98100449aa12fd3dd43952d62
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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