HCID 11179912, compound → HCID 11373744, compound

HRID 1358491Notes

Reaction equation

HRID 1358491 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][CH2:19][C@@H:20]([N:30]2[CH:34]=[C:33]([C:35]([NH2:37])=[O:36])[N:32]=[CH:31]2)[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:11][CH:10]=1)C1C=CC=CC=1>C1CCCCC=1.C(O)C.[OH-].[OH-].[Pd+2]>[Si:23]([O:22][CH2:21][C@H:20]([N:30]1[CH:34]=[C:33]([C:35]([NH2:37])=[O:36])[N:32]=[CH:31]1)[CH2:19][CH2:18][N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([OH:8])[CH:17]=2)[CH:13]=[CH:14]1)([C:26]([CH3:29])([CH3:27])[CH3:28])([CH3:24])[CH3:25]

Participants

5

Reactant 1

HCID 11179912HCID 11179912, compound

Product 1

HCID 11373744HCID 11373744, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

To a solution of 1-[(R)-4-(6-Benzyloxyindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (975 mg, 1.88 mmol) in cyclohexene (10 ml) and ethanol (20 ml) was added 20% palladium hydroxide on carbon (488 mg). The resulting mixture was stirred at reflux for 1 hour. After cooling to room temperature, the mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (20 g) chromatography eluted with chloroform/methanol (100:1 to 50:1) to give 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-hydroxyindol-1-yl)-2-butyl]imidazole-4-carboxamide (772 mg, 95.8%) as a colorless solid.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationthe mixture was filtered through Celite
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel (20 g) chromatography
  6. washeluted with chloroform/methanol (100:1 to 50:1)

Sources & evidence

ORD record
ord-774063a1be884780a6e34b6ec9a57855
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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