Water → 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoic acid

HRID 533552Notes

Reaction equation

HRID 533552 reaction equation
[CH3:1][C:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][CH:18]=[N:17]2)=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].O.[OH-].[Li+].O>O1CCCC1.CO.Cl>[CH3:1][C:2]([S:21]([CH3:24])(=[O:22])=[O:23])([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH:20]=[CH:19][CH:18]=[N:17]2)=[CH:14][CH:15]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66577932ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoate

Product 1

HCID 665779152-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoate (316 mg, 0.902 mmol) in tetrahyrofuran/methanol (4:1, 10 mL) was added a solution of lithium hydroxide monohydrate in water (1.8 M, 3.61 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with aqueous 1N HCl and extracted with ether 2×. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to afford 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoic acid as an oil. 286 mg. LCMS: (M−1) 321.3.

Workup

  1. extractionextracted with ether 2×
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8d4627ddd3754128834ab383bc51e73c
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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