Sodium Hydroxide → HCID 23373439, compound

HRID 1899418Notes

Reaction equation

HRID 1899418 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-d9451cb457b3495eaed508d86b64744f
Source dataset
uspto-grants-1996_11
Patent number
US05571925

Reaction notes

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