C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][NH:20]3)=[CH:16][CH:15]=2)=[O:11])=[CH:6][C:5]=1[Cl:23].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:23][C:5]1[CH:6]=[C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][NH:20]3)=[CH:16][CH:15]=2)=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:24])=[O:2]A solution of 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid methyl ester (Example 80; 2.00 g, 5.9 mmol) in tetrahydrofuran/methanol (1:1; 10 mL) was added to a solution of lithium hydroxide monohydrate (491 mg, 11.7 mmol) in water (5 mL). The solution was allowed to stir at room temperature for 72 h and then concentrated under reduced pressure to remove tetrahydrofuran and methanol. The remaining solution was diluted with water and acidified with 1N hydrochloric acid solution. The resulting mixture was extracted with ethyl acetate and the organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to afford 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid (1.90 g, 99% yield) as a colorless solid.
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