Potassium Hydroxide → (2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoic acid

HRID 2405920Notes

Reaction equation

HRID 2405920 reaction equation
[CH3:1][C@@:2]([S:22]([CH3:25])(=[O:24])=[O:23])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH3:21])=[N:11]1)[C:3]([O:5]CC)=[O:4].[OH-].[K+]>C1COCC1.CO.O>[CH3:1][C@@:2]([S:22]([CH3:25])(=[O:23])=[O:24])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH3:21])=[N:11]1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86710234ethyl (2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoate

Product 1

HCID 70817777(2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoic acidYield 78.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of the ethyl (2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoate (178 mg, 0.488 mmol, 1 eq) in THF: Methanol:water (2:2:1, 5 mL) was added potassium hydroxide (170 mg, 3.03 mmol) and reaction was stirred at RT overnight. The reaction was concentrated, and the residue was dissolved in aqueous 1N sodium hydroxide (20 mL) and washed with ethyl acetate (3×20 mL). The aqueous layer was acidified using concentrated HCl, and extracted with ethyl acetate (3×50 mL). The combined organics extracts were dried (MgSO4), filtered, and concentrated to afford (2R)-2-methyl-4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoic acid (129 mg, 78.6%). LC-MS M+H+382.1.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in aqueous 1N sodium hydroxide (20 mL)
  3. washwashed with ethyl acetate (3×20 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organics extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcee806434654974acfff1de314345c8
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

Loading…