HCID 57159292, compound → HCID 12970019, compound

HRID 278488Notes

Reaction equation

HRID 278488 reaction equation
C([O:8][C@H:9]([CH:11]([N:20]1[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:10])C1C=CC=CC=1>C1CCCCC=1.C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]([CH:11]([N:20]1[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:10]

Participants

5

Reactant 1

HCID 57159292HCID 57159292, compound

Product 1

HCID 12970019HCID 12970019, compoundYield 85.9%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

Twenty percent palladium hydroxide on carbon (30 mg) was added to a stirred solution of 1-[(2S)-2-benzyloxy-5-phenyl-3-pentyl]imidazole-4-carboxamide (obtained in Example 3(1))(107 mg) in cyclohexene (5 ml) and ethanol (12.5 ml). The resulting mixture was stirred at reflux temperature for 12 hours. After cooling to room temperature, the mixture was filtered through Celite, and the insoluble material on the filter was washed with ethanol. The filtrate and washing were combined and then concentrated in vacuo. The resulting residue was purified by silica gel (3 g) chromatography eluted with chloroform/methanol (50:1) to give 1-[(2S)-2-hydroxy-5-phenyl-3-pentyl]imidazole-4-carboxamide (69.1 mg).

Workup

  1. temperatureat reflux temperature for 12 hours
  2. filtrationthe mixture was filtered through Celite
  3. washthe insoluble material on the filter was washed with ethanol
  4. washThe filtrate and washing
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel (3 g) chromatography
  7. washeluted with chloroform/methanol (50:1)

Sources & evidence

ORD record
ord-8dae8d6c56fa4a7a88cafbd0d71b3bc6
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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