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

HRID 1930996Notes

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-91e6b926e2764a9fb7e0b9be90c93b62
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188139B2

Reaction notes

Loading…