Hydrochloric Acid → HCID 70817706, compound

HRID 2405937Notes

Reaction equation

HRID 2405937 reaction equation
[CH3:1][C@@:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH:12]=[N:11]1)[C:3]([O:5]CC)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][C@@:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH:12]=[N:11]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86710244HCID 86710244, compound

Product 1

HCID 70817706HCID 70817706, compoundYield 101.2%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]butanoate (0.078 g, 0.19 mmol) in THF-H2O (20 mL:10 mL) was added LiOH (0.047 g, 1.94 mmol, 10 eq). The mixture was allowed to stir at room temperature overnight. The mixture was acidified with 1M HCl and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to give (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]butanoic acid (0.072 g, 99% yield) as a white solid. LC-MS M+H+375.1.

Workup

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

Sources & evidence

ORD record
ord-062f8634f7af4b6abf9789b8b6b51ddd
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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