Sodium Hydroxide → HCID 23373439, compound

HRID 1461097Notes

Reaction equation

HRID 1461097 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[N:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:28])[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH3:15])[N:8]=[CH:7]1)C.[OH-].[Na+]>CO>[CH2:29]([CH:5]([N:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:28])[C:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH3:15])[N:8]=[CH:7]1)[C:4]([OH:35])=[O:3])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54504604HCID 54504604, compound

Product 1

HCID 23373439HCID 23373439, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6 g of α-hexyl-4-[(1-oxo-2,2-diphenylbutyl)amino]-1H-imidazole-1-acetic acid ethyl ester, 50 ml of 1N sodium hydroxide, and 100 ml of methanol were stirred at room temperature for 1 hour. The mixture was concentrated in vacuo, taken up in water, and the pH adjusted to 4.0. The aqueous solution was extracted with ethyl acetate. The organic extract was washed twice with water, dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved in methylene chloride, filtered, and concentrated in vacuo to provide 2.4 g of the desired titled product.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed twice with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4408fc9a8a29470c8c723b1ed276fc7c
Source dataset
uspto-grants-1991_12
Patent number
US05073566

Reaction notes

Loading…