Sodium Hydroxide → Rac-5-methylsulfamoyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid

HRID 225715Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To 1.6 mmol rac-5-methylsulfamoyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid methyl ester in 10 ml THF was added 20 mmol 2 M aq NaOH and the mixture was heated at 50° C. for 2 h. The mixture was then cooled to RT and extracted twice with ether. The aqueous phase was acidified with 10% aq citric acid and extracted twice with ethyl acetate. The combined organic phases were dried with Na2SO4. Evaporation in vacuo followed by trituration in ether and hexane afforded the title compound MS (m/e): 326.2 ([M−H]−, 100%)

Workup

temperatureThe mixture was then cooled to RT
extractionextracted twice with ether
extractionextracted twice with ethyl acetate
dry with materialThe combined organic phases were dried with Na2SO4
customEvaporation in vacuo

Sources & evidence

ORD record: ord-8f3492a55302429991e852a81e73b72a
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Reaction notes

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