Lithium hydroxide, monohydrate → HCID 58198418, compound

HRID 545317Notes

Reaction equation

HRID 545317 reaction equation
C([O:3][C:4](=[O:21])[C:5]([CH3:20])([S:7]([C:10]1[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)(=[O:9])=[O:8])[CH3:6])C.O.[OH-].[Li+]>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:20][C:5]([S:7]([C:10]1[CH:11]=[N:12][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:14][CH:15]=1)(=[O:8])=[O:9])([CH3:6])[C:4]([OH:21])=[O:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58198431HCID 58198431, compound

Product 1

HCID 58198418HCID 58198418, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

To a solution of 7.67 g (23.6 mmol) of 2-methyl-2-(6-trifluoromethyl-pyridine-3-sulfonyl)-propionic acid ethyl ester in THF/water (1/1, 200 mL) were added 1.97 g (46.9 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The organic solvent was removed under reduced pressure and the aqueous layer washed with diethyl ether (200 mL). The basic aqueous layer was cooled in an ice bath and acidified with 2M aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with ethyl acetate (4×200 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 6.34 g of 2-methyl-2-(6-trifluoromethyl-pyridine-3-sulfonyl)-propionic acid.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. washthe aqueous layer washed with diethyl ether (200 mL)
  3. temperatureThe basic aqueous layer was cooled in an ice bath
  4. extractionThe acidic aqueous layer was extracted with ethyl acetate (4×200 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-da395dcd5b6f42a58673a28ac51d797c
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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