tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → Ethyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

HRID 265143Notes

Reaction equation

HRID 265143 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:15][O:16][CH2:17][CH3:18])[NH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[C:25]([O:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:45]=[CH:44][C:41]([CH2:42][N:8]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[N:6]=[C:7]2[CH2:15][O:16][CH2:17][CH3:18])=[CH:40][CH:39]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178467660HCID 178467660, compound

Product 1

HCID 19036121Ethyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylateYield 93.4%

Procedure

A procedure similar to that described in Example 82(a) was repeated, except that 315 mg of ethyl 4-(1-hydroxy-1-methylethyl)-2-ethoxymethylimidazole-5-carboxylate [prepared as described in Preparation 44 (iii)], 145 mg of potassium t-butoxide and 510 mg of 4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide were employed and the product was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to obtain 600 mg of the title compound as a syrup.

Workup

  1. customthe product was purified by column chromatography through silica gel using a 1:1
  2. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3c1c1b887dba46edbea8838777b07090
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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