HCID 66813268, compound → HCID 57421290, compound

HRID 1097937Notes

Reaction equation

HRID 1097937 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-03d9cbb984d84277a11cded58cd33c31
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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