Lithium hydroxide, monohydrate → 2-Methyl-2-(pyridine-3-sulfonyl)-propionic acid

HRID 545310Notes

Reaction equation

HRID 545310 reaction equation
C([O:3][C:4](=[O:17])[C:5]([CH3:16])([S:7]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8])[CH3:6])C.O.[OH-].[Li+]>C1COCC1.O.O>[CH3:16][C:5]([S:7]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:17])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 581984122-Methyl-2-(pyridine-3-sulfonyl)-propionic acid ethyl ester

Product 1

HCID 581984762-Methyl-2-(pyridine-3-sulfonyl)-propionic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 240 mg (0.93 mmol) of 2-methyl-2-(pyridine-3-sulfonyl)-propionic acid ethyl ester in THF/water (4/1, 10 mL) were added 76 mg (1.8 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The reaction was further diluted with water (20 mL) and then washed with DCM (2×15 mL). The basic aqueous layer was cooled in an ice bath and acidified with 1M aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with isopropanol/chloroform (1/1, 3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 213 mg of 2-methyl-2-(pyridine-3-sulfonyl)-propionic acid.

Workup

  1. washwashed with DCM (2×15 mL)
  2. temperatureThe basic aqueous layer was cooled in an ice bath
  3. extractionThe acidic aqueous layer was extracted with isopropanol/chloroform (1/1, 3×20 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-273150149a0e4096931a7c0cc834eb5e
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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