Acetic Acid → HCID 57410854, compound

HRID 623871Notes

Reaction equation

HRID 623871 reaction equation
[CH3:1][C:2]([CH3:30])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][N:25]=3)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+].C(O)(=O)C>O1CCCC1.CO>[CH3:1][C:2]([CH3:30])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][N:25]=3)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67975438HCID 67975438, compound

Product 1

HCID 57410854HCID 57410854, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (0.85 mL) and methanol (0.85 mL) was dissolved methyl 2,2-dimethyl-3-(4-{5-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)propanoate (85 mg), 2N aqueous sodium hydroxide solution (1013.35 μL) was added to the solution, and the mixture was stirred at room temperature overnight. Acetic acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. To the residue were added acetic acid, water, and a phosphate buffer (pH 6.8), and after stirring the mixture, the organic layer was separated and concentrated under reduced pressure. After purification of the residue by LC-MS, it was dissolved in water and ethyl acetate, and the liquids were separated by adding 0.1 N phosphate buffer (pH 7.0). The organic layer was separated and concentrated under reduced pressure, and the obtained residue was pulverized by cooled ethyl acetate and collected by filtration to obtain 2,2-dimethyl-3-(4-{5-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)propanoic acid (29.3 mg).

Workup

  1. additionwas added to the solution
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionTo the residue were added acetic acid, water
  4. stirringa phosphate buffer (pH 6.8), and after stirring the mixture
  5. customthe organic layer was separated
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification of the residue by LC-MS, it
  8. dissolutionwas dissolved in water
  9. customethyl acetate, and the liquids were separated
  10. additionby adding 0.1 N phosphate buffer (pH 7.0)
  11. customThe organic layer was separated
  12. concentrationconcentrated under reduced pressure
  13. temperatureby cooled ethyl acetate
  14. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3520e636255244499dc78d80fab7b279
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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