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 53005Notes

Reaction equation

HRID 53005 reaction equation
C(OC[CH2:5][C:6]1[NH:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[N:10]=1)C.[CH3:20][C:21](C)([O-:23])C.[K+].[C:26]([O:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:46]=[CH:45][C:42]([CH2:43][N:7]2[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11]([OH:14])([CH3:12])[CH3:13])[N:10]=[C:6]2[CH2:5][O:23][CH2:21][CH3:20])=[CH:41][CH:40]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178467754HCID 178467754, compound

Product 1

HCID 19036121Ethyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylateYield 98.5%

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-3117d63b85964a4693aa3513158d8686
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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