5-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole → Ethyl 2-ethylthio-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 53017Notes

Reaction equation

HRID 53017 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([S:9][C:10]1[NH:11][C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[N:14]=1)[CH3:8].[C:24]([N:43]1[C:47]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:54]2[CH:61]=[CH:60][C:57]([CH2:58]Br)=[CH:56][CH:55]=2)=[N:46][N:45]=[N:44]1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C(=O)C>[CH2:7]([S:9][C:10]1[N:11]([CH2:58][C:57]2[CH:56]=[CH:55][C:54]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=3[C:47]3[N:43]([C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:44]=[N:45][N:46]=3)=[CH:61][CH:60]=2)[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([OH:18])([CH3:16])[CH3:17])[N:14]=1)[CH3:8]

Participants

5

Reactant 3

HCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 23665647Potassium tert-butoxideHCID 178470405HCID 178470405, compound

Product 1

HCID 19036180Ethyl 2-ethylthio-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

478 mg of potassium t-butoxide were added to a solution of 1.00 g of ethyl 2-ethylthio-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate [prepared as described in Preparation 50(ii)] in 20 ml of N,N-dimethylacetamide, whilst ice-cooling, and the mixture was stirred for 30 minutes. At the end of this time, 2.59 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide were added in portions to the mixture. Following a procedure similar to that described in Example 105(a) and purifying the residue by column chromatography through silica gel using a 1:5 by volume mixture of ethyl acetate and hexane as the eluent, 2.22 g of the title compound were obtained as an amorphous powder.

Workup

  1. temperaturecooling
  2. custompurifying the residue by column chromatography through silica gel using a 1:5
  3. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-9ede9d77a2554070991775681495cd35
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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