Hydrochloric Acid → Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.Cl.B([O-])([O-])[O-]>C1COCC1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[B:20]([OH:25])[OH:21])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
N-tert-Butylbenzenesulfonamide (2.00 g, 12.7 mmol) was dissolved in anhydrous THF (10 mL). After being cooled to −78° C., n-BuLi (2.5 M, 6.0 mL) was injected slowly to the above solution. After being stirred at this temperature for another 1 h, triisopropyl borate (11.9 g, 63.5 mmol) was added at −78° C. The resulting mixture was then allowed to warm to room temperature slowly for 8 h. 1N HCl (10 mL) was added to hydrolyze the borate. The organic layer was dried over Na2SO4. After removal of the solvent, the residue was used for the next step without further purification.
Workup
- temperatureto warm to room temperature slowly for 8 h
- dry with materialThe organic layer was dried over Na2SO4
- customAfter removal of the solvent
- customthe residue was used for the next step without further purification
Sources & evidence
- ORD record
- ord-3cfd9acada734cf8bf7ed8b74aadf9f0
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090628B2
Reaction notes
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