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

HRID 265145Notes

Reaction equation

HRID 265145 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:16][O:17][CH2:18][CH2:19][CH3:20])[NH:8][C:9]=1[C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[C:27]([O:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]1[CH:47]=[CH:46][C:43]([CH2:44][N:8]2[C:9]([C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])=[C:5]([C:2]([OH:1])([CH3:4])[CH3:3])[N:6]=[C:7]2[CH2:16][O:17][CH2:18][CH2:19][CH3:20])=[CH:42][CH:41]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178459025HCID 178459025, compound

Product 1

HCID 19036074Propyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propoxymethylimidazole-5-carboxylateYield 75.6%

Procedure

Following a procedure similar to that described in Example 82(a), but using 0.20 g of propyl 4-(1-hydroxy-1-methylethyl)-2-propoxymethylimidazole-5-carboxylate [prepared as described in Preparation 45(iii)], 82 mg of potassium t-butoxide and 290 mg of 4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide and then purifying the product by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, 293 mg of the title compound were obtained as a syrup.

Workup

  1. custompurifying the product 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-9cb0eb46b0d9462fb3f5c1e2abb6f2a7
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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