Hydrochloric Acid → 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

HRID 623888Notes

Reaction equation

HRID 623888 reaction equation
CO.[CH3:3][C:4]([CH3:41])([CH2:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]([C:23]3[N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:27]=3)=[CH:21][CH:22]=2)=[C:13]([CH3:40])[CH:12]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>C(OCC)(=O)C.O1CCCC1>[CH3:3][C:4]([CH3:41])([CH2:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]([C:23]3[N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[CH:25]=[C:26]([C:28]([F:29])([F:31])[F:30])[N:27]=3)=[CH:21][CH:22]=2)=[C:13]([CH3:40])[CH:12]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67975318methyl 2,2-dimethyl-3-({4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)propanoate

Product 1

HCID 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 acidYield 83.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Methanol (0.7 mL) and tetrahydrofuran (0.7 mL) were added to methyl 2,2-dimethyl-3-({4-methyl-6′-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)propanoate (99 mg), and after adding 2N aqueous sodium hydroxide solution (0.7 mL) to the mixture, the resulting mixture was stirred at 50° C. for 2 hours. To the reaction mixture was added ethyl acetate, and the mixture was neutralized by 2N hydrochloric acid. The organic layer was separated, washed with a saturated brine, and the residue obtained by concentrating the mixture under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=76:24 to 0:100) to obtain 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 (81 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated brine
  3. customthe residue obtained
  4. concentrationby concentrating the mixture under reduced pressure
  5. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=76:24 to 0:100)

Sources & evidence

ORD record
ord-91cfc724167f4ec49f78c6078d450973
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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