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

HRID 491542Notes

Reaction equation

HRID 491542 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 afford (3-ethylsulfamoyl-phenyl)-acetic acid as a solid (0.25 g, 1.1 mmol 99% yield). 1H NMR (DMSO-d6) 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

Sources & evidence

ORD record
ord-68909f950d8e4340891bd6c1680437aa
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Reaction notes

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