N-t-butyl-3-benzoyloxy-1-pentanesulfonamide → 3-Benzoyloxy-1-pentanesulfonamide
Reaction equation
C([NH:5][S:6]([CH2:9][CH2:10][CH:11]([O:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:12][CH3:13])(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:15]([O:14][CH:11]([CH2:12][CH3:13])[CH2:10][CH2:9][S:6]([NH2:5])(=[O:8])=[O:7])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-t-butyl-3-benzoyloxy-1-pentanesulfonamide (90.4 g) and trifluoroacetic acid (200 ml) was stirred overnight at room temperature. Trifluoroacetic acid was removed under reduced pressure and water and chloroform were added to the residue. A saturated aqueous solution of sodium hydrogencarbonate was added thereto with vigorously stirring until the aqueous layer became neutral. After extraction with chloroform, the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=2/1 to 1/1) to obtain 3-benzoyloxy-1-pentanesulfonamide (60.6 g) as oil.