Lithium hydroxide, monohydrate → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylic acid

HRID 265087Notes

Reaction equation

HRID 265087 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26]([O:28]C)=[O:27])=[C:24]([CH:30]([OH:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[C:22]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26]([OH:28])=[O:27])=[C:24]([CH:30]([OH:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[C:22]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 19036062Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylate

Product 1

HCID 190361551-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylic acidYield 86.2%

Procedure

Following a procedure similar to that described in Example 4, 0.87 g of methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylate [prepared as described in step (b) above] was hydrolyzed, using 342 mg of lithium hydroxide monohydrate, to afford 0.73 g of the title compound as crystals, melting at 199°-201° C. (with decomposition).

Sources & evidence

ORD record
ord-054e8300aba34a31be94ad934affce1c
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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