Hydrochloric Acid → HCID 70817543, compound

HRID 2405940Notes

Reaction equation

HRID 2405940 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20]CC)=[O:19])[CH:14]=1.[OH-].[Li+].Cl>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([OH:20])=[O:19])[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86710246HCID 86710246, compound

Product 1

HCID 70817543HCID 70817543, compoundYield 94%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoate (0.482 g, 1.23 mmol) in THF/H2O (20 mL:10 mL) was added lithium hydroxide (0.295 g, 12.3 mmol, 10 eq). The mixture was allowed to stir at RT 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)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (0.420 g, 94% yield) as a white solid. LC-MS M+H+364.1.

Workup

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

Sources & evidence

ORD record
ord-f12bfaeb1c6b407f8e9ba70fb7ad29f6
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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