Lithium hydroxide, monohydrate → (3-Ethylsulfamoyl-phenyl)-acetic acid

HRID 2108727Notes

Reaction equation

HRID 2108727 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11](=[O:16])(=[O:15])[NH:12][CH2:13][CH3:14])[CH:6]=1.O[Li].O>C1COCC1.O.C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:13]([NH:12][S:11]([C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:17])=[O:2])[CH:10]=[CH:9][CH:8]=1)(=[O:16])=[O:15])[CH3:14]

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57421970(3-Ethylsulfamoyl-phenyl)-acetic acid methyl ester

Product 1

HCID 57421971(3-Ethylsulfamoyl-phenyl)-acetic acidYield 99%

Reagents, catalysts & solvents 4

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Ethylsulfamoyl-phenyl)-acetic acid methyl ester (0.28 g, 1.1 mmol) was dissolved in THF and LiOH hydrate (63 mg, 1.5 mmol) in water was added. The reaction mixture was stirred at room temperature for 4 hours and then diluted with ethyl acetate and 10% citric acid. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to a solid. 0.25 g, 1.1 mmol 99% yield. 1H NMR 500 MHz (DMSO) 7.71 ppm, 1H, s; 7.70 ppm, 1H, m; 7.50 ppm, 3H, m; 4.11 ppm, 1H, br s; 3.70 ppm, 2H, s; 2.81 ppm, 2H, m; 0.99 ppm, 3H, t.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-94ac38098308457683554da4a2bcb3a8
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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