Sodium Hydroxide → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-[1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carboxamide

HRID 52939Notes

Reaction equation

HRID 52939 reaction equation
[OH-:1].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:27]([C:28]#[N:29])=[C:26]([C:30]([OH:37])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[N:25]=[C:24]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:18][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:27]([C:28]([NH2:29])=[O:1])=[C:26]([C:30]([OH:37])([CH:31]([CH3:33])[CH3:32])[CH:34]([CH3:35])[CH3:36])[N:25]=[C:24]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:18][CH:17]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 190361471-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carbonitrile

Product 1

HCID 190360781-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-[1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 500 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-[1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carbonitrile [prepared as described in step (a) above] in 10 ml of ethanol, and the resulting mixture was heated under reflux for 20 hours. At the end of this time, the reaction mixture was worked up in a similar manner to that described in Example 45(c), to give 220 mg of the title compound as an amorphous solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 20 hours

Sources & evidence

ORD record
ord-d8d4e3d6c68b4d9d8fa6dc6611d80647
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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