Hydrochloric Acid → HCID 178426556, compound

HRID 1514987Notes

Reaction equation

HRID 1514987 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25](=[O:35])[NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=4)=[CH:24][C:18]=3[N:17]=2)=[C:11]([CH3:36])[CH:10]=1)(C)(C)C.[OH-].[Na+].Cl>CO>[CH3:34][C:29]1[CH:28]=[C:27]([NH:26][C:25]([C:23]2[CH:22]=[CH:21][C:19]3[NH:20][C:16]([C:12]4[C:11]([CH3:36])=[CH:10][C:9]([CH2:8][CH2:7][C:6]([OH:37])=[O:5])=[CH:14][C:13]=4[CH3:15])=[N:17][C:18]=3[CH:24]=2)=[O:35])[CH:32]=[CH:31][C:30]=1[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178426557HCID 178426557, compound

Product 1

HCID 178426556HCID 178426556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-{4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid tert-butyl ester (120 mg) in MeOH (5 mL) was added 1N NaOH solution (5 mL). The mixture was stirred at room temperature for 18 h then the aqueous layer was carefully acidified to pH=2-3 with 1N HCl. The resulting suspension was filtered, washed with water and dried to give 3-{4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid as red solid. MS (ESI)m/z 442 (M+H). 1H NMR (MeOD, 400 MHz) δ 8.37 (s, 1H), 8.14 (d, 1H), 7.90 (d, 1H), 7.48 (s, 1H), 7.44 (dd, 1H), 7.21 (s, 2H), 7.14 (d, 1H), 2.97 (t, 2H), 2.67 (t, 2H), 2.30 (s, 3H), 2.27 (s, 3H), 2.10 (s, 6H).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4c89b29fd91a4824a9c47f8688e960fa
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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