Sodium Hydroxide → 4'-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic Acid

HRID 424825Notes

Reaction equation

HRID 424825 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[N:20]([C:27]4[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:34])[N:21]=[N:22][C:23]=3[CH:24]([CH3:26])[CH3:25])=[CH:13][C:12]=2[CH3:35])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[N:20]1[C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=3)=[C:12]([CH3:35])[CH:13]=2)=[C:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[N:21]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 667041164'-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 576527434'-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic AcidYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4′-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2′-methyl-biphenyl-4-carboxylic acid methyl ester (4.55 g, 1 equiv) and 1N NaOH (44.6 mL, 5 equiv) in MeOH (200 mL) is heated to 75° C. for 1 h. The reaction mixture is cooled to room temperature and is concentrated under reduced pressure. The residue is dissolved in water (200 mL) and the solution is acidified with 5N HCl. The resulting precipitate is filtered and dried under reduced pressure to give the title compound (4.21 g, 95%). ES/MS m/e (35Cl/37Cl) 496.3/498 (M+1).

Workup

  1. concentrationis concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in water (200 mL)
  3. filtrationThe resulting precipitate is filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7865ce9d6e3947b08cafc5ba4ebda2bb
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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