Sodium Hydroxide → 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoic acid

HRID 273359Notes

Reaction equation

HRID 273359 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=[C:21]2[C:29]([F:32])([F:31])[F:30])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>CCO.O>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=[C:21]2[C:29]([F:30])([F:31])[F:32])=[CH:15][CH:16]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11851905ethyl 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoate

Product 1

HCID 116974862-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoic acidYield 79.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoate (238.5 mg, 0.5 mmol) in EtOH (5 ml) was added NaOH (2 ml, 2M aq. Solution, 2 mmol) in water (2 ml) at 0° C. at once. The reaction mixture was stirred at RT until all the ester disappeared (TLC). EtOH was removed in vacuo and the residue was dissolved in water. The solution was acidified to pH4 using 3N HCl and the precipitated acid was extracted with EtOAc to give the product as white solid (167 mg, 77.3%).

Workup

  1. customEtOH was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionthe precipitated acid was extracted with EtOAc

Sources & evidence

ORD record
ord-f67487f36bcc4fb9aa16b73d597058a3
Source dataset
uspto-grants-2008_11
Patent number
US07456293B2

Reaction notes

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