Tert-butyl 2,2-dimethyl-3-[2-methyl-4-[5-[4-(trifluoromethyl)-1-(2-trimethylsilylethoxymethyl)-imidazol-2-yl]-2-pyridyl]phenoxy]propanoate → 2,2-dimethyl-3-[2-methyl-4-[5-[5-(trifluoromethyl)-1H-imidazol-2-yl]-2-pyridyl]phenoxy]propanoic acid

HRID 623880Notes

Reaction equation

HRID 623880 reaction equation
[CH3:1][C:2]([CH3:42])([CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:25](COCC[Si](C)(C)C)[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)=[CH:20][N:19]=2)=[CH:14][C:13]=1[CH3:41])[C:3]([O:5]C(C)(C)C)=[O:4]>FC(F)(F)C(O)=O.O>[CH3:1][C:2]([CH3:42])([CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[NH:28][C:27]([C:29]([F:32])([F:30])[F:31])=[CH:26][N:25]=3)=[CH:20][N:19]=2)=[CH:14][C:13]=1[CH3:41])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 86698168Tert-butyl 2,2-dimethyl-3-[2-methyl-4-[5-[4-(trifluoromethyl)-1-(2-trimethylsilylethoxymethyl)-imidazol-2-yl]-2-pyridyl]phenoxy]propanoate

Product 1

HCID 679754222,2-dimethyl-3-[2-methyl-4-[5-[5-(trifluoromethyl)-1H-imidazol-2-yl]-2-pyridyl]phenoxy]propanoic acidYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In trifluoroacetic acid (5 mL) and water (0.5 mL) was dissolved tert-butyl 2,2-dimethyl-3-[2-methyl-4-[5-[4-(trifluoromethyl)-1-(2-trimethylsilylethoxymethyl)-imidazol-2-yl]-2-pyridyl]phenoxy]propanoate (103 mg), and the mixture was stirred at room temperature overnight. The residue obtained by concentrating the reaction mixture under reduced pressure was dissolved in tetrahydrofuran, and 1N aqueous sodium hydroxide solution was added to the mixture to adjust a pH thereof to 7. To the mixture were added 0.1N phosphate buffer, ethyl acetate and water, and the liquids were separated. The organic layer was separated, dried over anhydrous sodium sulfate, and ether was added to the residue obtained by concentrating the solution under reduced pressure to pulverize the precipitates to obtain 2,2-dimethyl-3-[2-methyl-4-[5-[5-(trifluoromethyl)-1H-imidazol-2-yl]-2-pyridyl]phenoxy]propanoic acid (59.1 mg).

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. dissolutionwas dissolved in tetrahydrofuran
  4. addition1N aqueous sodium hydroxide solution was added to the mixture
  5. additionTo the mixture were added 0.1N phosphate buffer, ethyl acetate and water
  6. customthe liquids were separated
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate, and ether
  9. additionwas added to the residue
  10. customobtained
  11. concentrationby concentrating the solution under reduced pressure
  12. customprecipitates

Sources & evidence

ORD record
ord-b70eb4fabf764161b4da230eaa681da3
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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