Ethyl Acetate → Ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 265131Notes

Reaction equation

HRID 265131 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][CH2:10][C:11]1[NH:12][C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[N:15]=1)[CH3:8].[C:25]([N:44]1[C:48]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[C:55]2[CH:62]=[CH:61][C:58]([CH2:59]Br)=[CH:57][CH:56]=2)=[N:47][N:46]=[N:45]1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>CN(C)C(=O)C.O>[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:59][C:58]2[CH:57]=[CH:56][C:55]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=3[C:48]3[N:44]([C:25]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:45]=[N:46][N:47]=3)=[CH:62][CH:61]=2)[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([C:16]([OH:19])([CH3:17])[CH3:18])[N:15]=1)[CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 23665647Potassium tert-butoxideHCID 178467660HCID 178467660, compound

Product 1

HCID 19036157Ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

217 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 450 mg of ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate [prepared as described in Preparation 44(iii)] in 5 ml of N,N-dimethylacetamide, and the mixture was stirred for 30 minutes. At the end of this time, a solution of 1.47 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours, after which it was mixed with ethyl acetate and water and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting 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 1.2 g of the title compound as an amorphous powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. stirringshaken
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting 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-423ae3cb5d8c43d685622b3699659bdd
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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