Water → Isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 265137Notes

Reaction equation

HRID 265137 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]([C:11]1[N:12]=[C:13]([CH2:22][O:23][CH:24]([CH3:26])[CH3:25])[NH:14][C:15]=1[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])([CH3:10])[CH3:9].[C:27]([N:46]1[C:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:57]2[CH:64]=[CH:63][C:60]([CH2:61]Br)=[CH:59][CH:58]=2)=[N:49][N:48]=[N:47]1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C(=O)C.C(OCC)(=O)C>[OH:7][C:8]([C:11]1[N:12]=[C:13]([CH2:22][O:23][CH:24]([CH3:26])[CH3:25])[N:14]([CH2:61][C:60]2[CH:59]=[CH:58][C:57]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=3[C:50]3[N:46]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:47]=[N:48][N:49]=3)=[CH:64][CH:63]=2)[C:15]=1[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 23665647Potassium tert-butoxideHCID 178459024HCID 178459024, compound

Product 1

HCID 19036290Isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

239 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 550 mg of isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethylimidazole-5-carboxylate [prepared as described in Preparation 46(iii)] in 6 ml of N,N-dimethylacetamide, and the resulting mixture was stirred for 30 minutes. A solution of 1.62 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was then added dropwise, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was mixed with water and ethyl acetate and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. 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 1.47 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-1e1df6de25304b3f802a0b3120f759b3
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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