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

HRID 53004Notes

Reaction equation

HRID 53004 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:14][O:15][CH3:16])[NH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[C:23]([O:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:43]=[CH:42][C:39]([CH2:40][N:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[N:6]=[C:7]2[CH2:14][O:15][CH3:16])=[CH:38][CH:37]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178494672Methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate

Product 1

HCID 19036170Methyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylateYield 93.9%

Procedure

Following a procedure similar to that described in Example 82(a), but using 230 mg of methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate [prepared as described in Preparation 42(v)], 119 mg of potassium t-butoxide and 420 mg of 4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide and then purifying the product by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, 468 mg of the title compound were obtained as a syrup.

Workup

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

Sources & evidence

ORD record
ord-7f16cd4f59bc4767a55ae3b5c60eb4cb
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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