Hydrochloric Acid → HCID 70817619, compound

HRID 2405916Notes

Reaction equation

HRID 2405916 reaction equation
[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:23])([S:19]([CH3:22])(=[O:21])=[O:20])[C:14]([O:16]CC)=[O:15])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl>O1CCOCC1>[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:23])([S:19]([CH3:22])(=[O:20])=[O:21])[C:14]([OH:16])=[O:15])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86710232HCID 86710232, compound

Product 1

HCID 70817619HCID 70817619, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoate (100 mg, 0.292 mmol) in dioxane (3 mL) was added a 2M LiOH solution (0.0876 mL, 1.75 mmol, 6 eq). The reaction was allowed to stir overnight at RT. The mixture was then acidified with 1M HCl. The aqueous phase was then extracted with EtOAc, dried (MgSO4), filtered, and concentrated in vacuo to give (2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (92 mg, 100% yield) which was used without further purification. LC-MS M+H+315.1.

Workup

  1. extractionThe aqueous phase was then extracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-503dffab7fb84aac8b0bb7e4ed94abeb
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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