Sodium Hydroxide → 2,2-dimethyl-3-({4-methyl-6'-[5-(trifluoromethyl)-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)propanoic acid

HRID 623889Notes

Reaction equation

HRID 623889 reaction equation
[CH3:1][C:2]([CH3:38])([CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][C:17]([C:20]3[N:21](COCC[Si](C)(C)C)[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:24]=3)=[CH:18][CH:19]=2)=[C:10]([CH3:37])[CH:9]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+]>FC(F)(F)C(O)=O.O>[CH3:1][C:2]([CH3:38])([CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][C:17]([C:20]3[NH:24][C:23]([C:25]([F:28])([F:26])[F:27])=[CH:22][N:21]=3)=[CH:18][CH:19]=2)=[C:10]([CH3:37])[CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 679732552,2-dimethyl-3-({4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)propanoic acid

Product 1

HCID 679752462,2-dimethyl-3-({4-methyl-6'-[5-(trifluoromethyl)-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)propanoic acidYield 49.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In trifluoroacetic acid (2.0 mL) and water (0.1 mL) was dissolved 2,2-dimethyl-3-({4-methyl-6′-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)propanoic acid (80 mg), and the solution was stirred at room temperature for 7 hours. To the solution was added 2N aqueous sodium hydroxide solution to make a pH of the same 2 to 3, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated brine, the organic layer was separated and concentrated under reduced pressure. Isopropyl ether was added to the obtained residue, and the precipitated solid was collected by filtration and dried under reduced pressure to obtain 2,2-dimethyl-3-({4-methyl-6′-[5-(trifluoromethyl)-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)propanoic acid (30 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated brine
  3. customthe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. additionIsopropyl ether was added to the obtained residue
  6. filtrationthe precipitated solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-07a69e2ab2724fcb9628126ed73af5c8
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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