Hydrochloric Acid → HCID 70817489, compound

HRID 2405943Notes

Reaction equation

HRID 2405943 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH2:17][C@@:18]([CH3:28])([S:24]([CH3:27])(=[O:26])=[O:25])[C:19]([O:21]CC)=[O:20])[CH:15]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Li+].Cl>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH2:17][C@@:18]([CH3:28])([S:24]([CH3:27])(=[O:25])=[O:26])[C:19]([OH:21])=[O:20])[CH:15]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86710248HCID 86710248, compound

Product 1

HCID 70817489HCID 70817489, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl (2R)-4-{4-[(3-cyanophenyl)ethynyl]-1H-pyrazol-1-yl}-2-methyl-2-(methylsulfonyl)butanoate (0.415 g, 1.04 mmol) in THF-H2O (20 mL:10 mL) was added lithium hydroxide (0.249 g, 10.4 mmol, 10 eq). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was then acidified with 1M HCl and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to give (2R)-4-{4-[(3-cyanophenyl)ethynyl]-1H-pyrazol-1-yl}-2-methyl-2-(methylsulfonyl)butanoic acid (0.360 g, 93% yield) as a white solid. LC-MS M+H+372.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f63a00c95abf46f0840ebe83508cec80
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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