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(2-Butyl-4-chloro-1-((2'-(1-trityl-1H-tetraazol-5-YL)(1,1'-biphenyl)-4-YL)methyl)-1H-imidazol-5-YL)methanol → N-Trityl Losartan Carboxaldehyde

HRID 487910
Notes
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Reaction equation

HRID 487910 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]>ClCCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 11643218(2-Butyl-4-chloro-1-((2'-(1-trityl-1H-tetraazol-5-YL)(1,1'-biphenyl)-4-YL)methyl)-1H-imidazol-5-YL)methanol

Product 1

HCID 11657587N-Trityl Losartan CarboxaldehydeYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 0.765 g of the product of Example 1 in 20 ml of 1,2-dichloroethane is sonicated under argon for 18 hours with 0.517 g of manganese dioxide. An additional 2 g of manganese dioxide is added and sonication continued for 2 hours. The reaction reaction mixture is filtered through diatomaceous earth which is washed with 500 ml of methylene chloride. The filtrate is concentrated in vacuo to give 0.696 g of the desired product as a solid. FAB MASS SPEC 685(M+Na).

Workup

  1. customsonication
  2. customThe reaction reaction mixture
  3. filtrationis filtered through diatomaceous earth which
  4. washis washed with 500 ml of methylene chloride
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-2cfb2998dd4b40e49709fbb5997cabbc
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05298517

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes