Sodium Hydroxide → 2-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid

HRID 412206Notes

Reaction equation

HRID 412206 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[CH3:28])C.[OH-].[Na+]>CO>[CH3:29][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:13]=[C:12]1[CH3:28])[C:4]([OH:30])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25190471ethyl 2-methyl-7-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)heptanoate

Product 1

HCID 185375322-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Scheme 3 (P)) A solution of starting material 2-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid ethyl ester (130 mg, 0.32 mmole) in Methanol (5 ml) and Sodium Hydroxide (64 mg, 1.61 mmole) was let stirred under reflux for 18 hrs. The next day, the reaction was let cooled to room temperature and concentrated in vacuo. The residue was diluted with water, and acidified with Hydrochloric Acid (3N). The aqueous layer was extracted with Dichloromethane (3×10 ml). The organic layers were combined, dried over Sodium Sulfate and filtered. The resultant filtrate was concentrated in vacuo to afford product as a white solid (120 mg, 99%). Mass Spec: 377 (MH+).

Workup

  1. temperatureunder reflux for 18 hrs
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionThe aqueous layer was extracted with Dichloromethane (3×10 ml)
  5. dry with materialdried over Sodium Sulfate
  6. filtrationfiltered
  7. concentrationThe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cbfc84c7caf14d519d84168d860f03db
Source dataset
uspto-grants-2003_05
Patent number
US06562846B2

Reaction notes

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