Sodium Hydroxide → 2-(4-Methoxy-benzyloxy)-5-sulfamoyl-benzoic acid

HRID 2251279Notes

Reaction equation

C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[OH-].[Na+]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:5]2[CH:6]=[CH:7][C:8]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:9][C:4]=2[C:3]([OH:24])=[O:2])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 2.5 mmol 2-(4-methoxy-benzyloxy)-5-sulfamoyl-benzoic acid methyl ester in 6 ml THF was added 5 mmol 2 M aq NaOH, and the mixture was heated at 60° C. for 30 min. The mixture was then cooled to RT and extracted twice with ethyl acetate. The aqueous phase was acidified to pH 1 with 5 M aq HCl and extracted with ethyl acetate. The combined organic phases were washed with saturated aq NaCl and dried with Na2SO4. Evaporation in vacuo afforded the title compound. MS (m/e): 336.1 ([M−H]−, 100%)

Workup

temperatureThe mixture was then cooled to RT
extractionextracted twice with ethyl acetate
extractionextracted with ethyl acetate
washThe combined organic phases were washed with saturated aq NaCl
dry with materialdried with Na2SO4
customEvaporation in vacuo

Sources & evidence

ORD record: ord-d1ba224c654540969b4691b291c59317
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319099B2

Reaction notes

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