Lithium Hydroxide → HCID 70817727, compound

HRID 2405911Notes

Reaction equation

HRID 2405911 reaction equation
[CH:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:15]([O-:17])=[O:16])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>CO.C1COCC1.O>[CH:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:22])([S:18]([CH3:21])(=[O:19])=[O:20])[C:15]([OH:17])=[O:16])[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86710229HCID 86710229, compound

Product 1

HCID 70817727HCID 70817727, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoate (87 mg, 0.24 mmol, 1 eq) in MeOH/THF (2 mL:2 mL) was added LiOH (21.5 mg, 0.512 mmol, 2.1 eq) in H2O (1 mL). The mixture was allowed to stir at RT overnight. The mixture was washed with Et2O and the aqueous layer acidified with 1M HCl. The solid precipitate was filtered off to give (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (70 mg, 87%) which was used without further purification. LC-MS M+H+329.1.

Workup

  1. washThe mixture was washed with Et2O
  2. filtrationThe solid precipitate was filtered off

Sources & evidence

ORD record
ord-b15f473d878c40eb900c7ac7e031613a
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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