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

HRID 1351016Notes

Reaction equation

HRID 1351016 reaction equation
C(OC(=O)C(C)CCCCC[C:11]1([CH3:28])[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12]1)C.[OH-:31].[Na+].[CH3:33][OH:34]>>[CH3:23][CH:22]([CH2:13][CH2:14][CH2:16][CH2:17][CH2:18][N:15]1[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:12]=[C:11]1[CH3:28])[C:33]([OH:34])=[O:31]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 694184432-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-2-yl)-heptanoic acid ethyl ester

Product 1

HCID 185375322-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acidYield 99%

Procedure

(Scheme 3 (P)) A solution of starting material 2-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-2-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-f8903ad01ab040dba0f0a680aa170aa9
Source dataset
uspto-grants-2007_05
Patent number
USRE039634E1

Reaction notes

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