Hydrochloric Acid → HCID 70817564, compound

HRID 2405924Notes

Reaction equation

HRID 2405924 reaction equation
[CH3:1][C@@:2]([S:14]([CH3:17])(=[O:16])=[O:15])([CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]1)[C:3]([O-:5])=[O:4].C1COCC1.CO.O.[Li+].[OH-].Cl>O>[CH3:1][C@@:2]([S:14]([CH3:17])(=[O:15])=[O:16])([CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 86710237HCID 86710237, compound

Product 1

HCID 70817564HCID 70817564, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (2R)-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoate (182 mg 0.455 mmol, 1 eq) in 2:2:1 THF-MeOH-water (6 mL) was added 0.1 M aq. LiOH and the reaction mixture was allowed to stir overnight at RT. The reaction mixture was concentrated under reduced pressure (to remove organics) to provide an aqueous solution, which was diluted with water (5 mL) and acidified to pH=2 with 1 M HCl. Upon acidification, a white precipitate formed, which was filtered, washed with water, and dried under reduced pressure to give (2R)-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoic acid. LC-MS M+H+261.1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure (to remove organics)
  2. customto provide an aqueous solution, which
  3. customUpon acidification, a white precipitate formed
  4. filtrationwhich was filtered
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c6e3791019a4e0e983d0877cc13a2d7
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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