[OH-].[Li+].[CH3:3][C:4]([O:7][C:8]([NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([O:22]C)=[O:21])[NH:17]2)=[CH:13][CH:12]=1)=[O:9])([CH3:6])[CH3:5].C1COCC1.CO>O>[CH3:6][C:4]([O:7][C:8]([NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([OH:22])=[O:21])[NH:17]2)=[CH:13][CH:12]=1)=[O:9])([CH3:3])[CH3:5]
Lithium hydroxide (0.095 g, 3.96 mmol) was added to a solution of methyl 6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.115 g, 0.396 mmol) in a 3:1:1 mixture of THF:methanol:water (2 ml). The reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was dissolved in water and acidified with 1N aqueous HCl. The resulting suspension was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and the solvent was evaporated to give the title compound (0.115 g, >99%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.18 (s, 1H), 9.21 (s, 1H), 7.70 (s, 1H), 7.37 (d, 1H), 6.93 (dd, 1H), 6.74 (s, 1H), 1.46 (s, 9H). MS: m/z 275 (M−1).
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