1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide → FR-234938

HRID 278496Notes

Reaction equation

HRID 278496 reaction equation
C([O:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10])C1C=CC=CC=1>C(O)C.C1CCCCC=1.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10]

Participants

5

Reactant 1

HCID 573241101-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide

Product 1

HCID 449013FR-234938Yield 68.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide (obtained in Example 17 or 20) (5.07 g) was dissolved in a mixture of ethanol (300 ml) and cyclohexene (150 ml) and then palladium hydroxide (20% on carbon, 5.0 g) was added. The mixture was heated under reflux for 3 days. After cooling, the catalyst was filtered and washed with ethanol. The combined filtrate and washings were concentrated in vacuo. Flash chromatography (dichloromethane:methanol=10:1) gave 1-[(2S,3R)-2-hydroxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide (2.71 g, 68.4%) as a foam.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 days
  3. temperatureAfter cooling
  4. filtrationthe catalyst was filtered
  5. washwashed with ethanol
  6. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-5cdf8c174561423dba1a58e98879c422
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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