tert-butyl 2-{1-{[(benzyloxy)carbonyl]amino}-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate → tert-butyl 2-{1-amino-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate

HRID 425385Notes

Reaction equation

HRID 425385 reaction equation
C(OC([NH:11][CH:12]([C:27]1[N:28]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:29]=[C:30]([CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][CH3:35])[N:31]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)=[CH:16][CH:15]=1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH:12]([C:27]1[N:28]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH:29]=[C:30]([CH2:32][C:33]([CH3:36])([CH3:37])[CH2:34][CH3:35])[N:31]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 66705640tert-butyl 2-{1-{[(benzyloxy)carbonyl]amino}-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate

Product 1

HCID 66705676tert-butyl 2-{1-amino-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd (10 wt % on activated carbon) (catalytic) was added to a degassed, ambient temperature solution of tert-butyl 2-{1-{[(benzyloxy)carbonyl]amino}-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate (63 mg, 0.1 mmol) in methanol (5 mL). After stirring at ambient temperature under an atmosphere of hydrogen for 4 h, the reaction mixture was filtered through cotton and concentrated in vacuo to afford tert-butyl 2-{1-amino-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate which was used in the subsequent step without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through cotton
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-527aff42782340c9b29f6c75c074ff13
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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