Hydrochloric Acid → 3-{[5-(Methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid
Reaction equation
[CH2:1]([N:4]([S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]CC[Si](C)(C)C)=[O:25])[CH:19]=1)(=[O:17])=[O:16])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([N:4]([CH2:1][CH2:2][CH3:3])[S:15]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:24]([OH:26])=[O:25])(=[O:16])=[O:17])=[N:6][CH:7]=1)=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 175 mg of methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate and 5 mL of THF was added dropwise a solution of TBAF in THF (1 M, 0.750 mL), followed by stirring at room temperature for 4 hours. To the reaction mixture was added 0.1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then dried under reduced pressure to obtain 110 mg of 3-{[5-(methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid as a colorless powder.
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-6a087f98146b4464807a48f237fff9d3
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729068B2
Reaction notes
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