N-(4-methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide → N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])(=[O:27])=[O:26])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:5][CH:4]=1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:26])=[O:27])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:7][CH:8]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
200 mg (0.34 mmol) N-(4-Methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide 9 were dissolved in 3.0 mL trifluoroacetic acid and stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure to give an yellow oil. The residue was purified by silica gel chromatography (eluent: methylene chloride/diethylether 6:4+0.1% acetic acid). Evaporation of the appropriate fractions gave 140 mg of the desired product 10.