Lithium hydroxide, monohydrate → 2-Methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid

HRID 553583Notes

Reaction equation

HRID 553583 reaction equation
C([O:3][C:4](=[O:16])[C:5]([CH3:15])([S:7]([CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:9])=[O:8])[CH3:6])C.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:15][C:5]([S:7]([CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:9])=[O:8])([CH3:6])[C:4]([OH:16])=[O:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 592532542-Methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid ethyl ester

Product 1

HCID 592532112-Methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acidYield 100%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 3.78 g (15.09 mol) of 2-methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid ethyl ester in THF/water (4/1, 50 mL) are added 1.58 g (37.74 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 18 h. The reaction mixture is concentrated under reduced pressure and the residue dissolved in DCM (20 mL) and extracted with water (50 mL). The aqueous layer is cooled in an ice bath and then acidified with 6M aqueous HCl solution to pH 1. The resulting precipitate is isolated by filtration, and dried under reduced pressure at 50° C. to afford 3.35 g of 2-methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid as white crystalline solids. Yield: 100%; ES-MS: m/z 221 [M−H].

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe residue dissolved in DCM (20 mL)
  3. extractionextracted with water (50 mL)
  4. temperatureThe aqueous layer is cooled in an ice bath
  5. customThe resulting precipitate is isolated by filtration
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-5771db6ba3b44224a12baf2dadc77789
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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