Trifluoroacetic acid → 2-((1H-indol-5-yl)amino)-4-phenylbenzoic acid
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:35]=[CH:34][C:26]=3[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=O)(C)(C)C>>[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:35]=[CH:34][C:26]=3[C:27]([OH:29])=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1Participants
3
Procedure
Trifluoroacetic acid 5 mL solution of the obtained tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((1H-indol-5-yl)amino)-4-phenylbenzoic acid 8 mg of yellow solid.
Workup
- customThe solvent was removed under reduced pressure