Sodium Hydroxide → HCID 66899666, compound

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Reaction Steps

3-{1-Benzenesulfonyl-3-[3,5-di-tert-butyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-1H-indol-5-yl}-but-2-enoic acid methyl ester was dissolved in methanol (1.5 mL)/dioxane (3 mL) and treated with 1N NaOH (2.0 mL) at 60° C. for 2.5 h. Diluted with 1N HCl (15 mL) and extracted with ethyl acetate (3×15 mL). The combined organic portions were washed with water (30 mL), brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to provide 145 mg of crude material. The material was purified using radial chromatography by (eluet: hexane/ethyl acetate gradient) to provide 72 mg (53%) of a pale yellow solid. Mp. 146-153° C. 1H NMR (250 MHz, CDCl3): δ 8.43 (bs, 1H), 7.95 (s, 1H), 7.53 (d, 1H, J=2.4), 7.46 (m, 3H), 7.38 (d, 1H, J=2.5), 6.26 (d, 1H, J=1.1), 3.86 (q, 2H, J=8.6), 2.69 (d, 3H, J=1.0), 1.49 (s, 9H), 1.37 (s, 9H). MS [EI+] 488 (M+H)+, [EI−] 486 (M−H)+. Analytical (C29H37NO3): Calculated C, 68.98; H, 6.62; N, 2.87. Found: C, 66.45; H, 6.85; N, 2.59.

Provenance & Evidence