Hydrochloric Acid → 3-{Ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid
Reaction equation
[CH2:1]([N:3]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=1)[S:4]([C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[C:10]([O:12]CC[Si](C)(C)C)=[O:11])(=[O:6])=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH2:1]([N:3]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=1)[S:4]([C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])(=[O:6])=[O:5])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 330 mg of 2-(trimethylsilyl)ethyl 3-{ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoate and 5.0 mL of THF was added a solution of TBAF in THF (1.0 M, 1.42 mL), followed by stirring at room temperature for 15 hours. To the reaction mixture was added a 0.1 M aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a 0.1 M aqueous hydrochloric acid solution and a 10% aqueous citric acid solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 238 mg of 3-{ethyl[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid as a white solid.
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with a 0.1 M aqueous hydrochloric acid solution
- dry with materiala 10% aqueous citric acid solution, and dried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1f4ab6e374ac47bd9692841669e21b9b
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284295B2
Reaction notes
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