Sodium Hydroxide → 5-(((tert-butoxy)carbonyl)amino)-1H-indole-2-carboxylic acid

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Reaction Steps

A solution of compound 30 (2.61 g, 8.6 mmol) in methanol (200 mL) was treated with 3N sodium hydroxide solution (50 mL) , and the reaction mixture was stirred for 18 h at room temperature. Solvent was removed. Water (100 mL) was added. The solution was neutralized with 20% hydrochloric acid and the precipitate was filtered to give compound 31 (2.03 g, 86%) as a yellow solid. m.p.192°-193° C. 1H NMR (DMSO-d6, ppm) 12.83 (brs, 1 H, COOH), 11.69 (s, 1 H, NH), 9.13 (s, 1 H, CONH), 7.79-7.04 (m, 4 H, Ar--H), 1.48 (s, 9 H, C(CH3)3). Anal. (C14H16N2O4 0.5H2 O), C, H, N.

Provenance & Evidence