HCID 66813268, compound → HCID 57421290, compound

HRID 333836Notes

Reaction equation

HRID 333836 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([OH:26])([C:22]([F:25])([F:24])[F:23])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[Cl:21])[CH3:13])[CH:8]=[CH:7][N:6]=1)=[O:4]>[OH-].[Li+].C1COCC1.CO>[Cl:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[CH:12]([CH3:13])[C:11]([C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=1)([OH:26])[C:22]([F:23])([F:24])[F:25]

Participants

5

Reactant 1

HCID 66813268HCID 66813268, compound

Product 1

HCID 57421290HCID 57421290, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(2-Chloro-4-fluoro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridine-2-carboxylic acid methyl ester (24 mg) was dissolved in an aqueous lithium hydroxide solution (1N, 5 ml), THF (5 ml), and methanol (2.5 ml). The mixture was stirred for 10 min. LCMS indicated complete hydrolysis. Volatile solvents were evaporated. The residue was diluted with water (10 ml) and washed with diethyl ether. The aqueous layer was acidified to about pH 4 with HCl (aq., 1N) and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (22 mg) as a white solid. MS (m/e)=378.2 [M+H+].

Workup

  1. customhydrolysis
  2. customVolatile solvents were evaporated
  3. additionThe residue was diluted with water (10 ml)
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34ab37a7c557438f971e408fda7d49d1
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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