Water → Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

HRID 265044Notes

Reaction equation

HRID 265044 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]([C:11]1[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[NH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:10])[CH3:9].Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1.O>CN(C)C(=O)C>[C:41]([O:40][C:38]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:14]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]([C:8]([OH:7])([CH3:10])[CH3:9])[N:12]=[C:13]2[CH2:21][CH2:22][CH3:23])=[CH:27][CH:28]=1)=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 962WaterHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178440079HCID 178440079, compound

Product 1

HCID 10625404Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

3.00 g of potassium t-butoxide were added, whilst ice-cooling, to a solution of 6 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 40 ml of N,N-dimethylacetamide, and the resulting mixture was stirred for 10 minutes, after which a solution of 9.00 g of t-butyl 4'-bromomethylbiphenyl -2-carboxylate in 40 ml of N,N-dimethylacetamide was added. After the reaction mixture had been stirred at room temperature for 1 hour and then at 50° C. for 2 hours, it was mixed with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure, after which the residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 11.6 g of the title compound as a solid, softening at above 85° C.

Workup

  1. stirringAfter the reaction mixture had been stirred at room temperature for 1 hour
  2. waitat 50° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customafter which the residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3b97032f4ec5463c968b278cb6791224
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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