Sodium Hydroxide → HCID 86594129, compound

Participants

Reaction Steps

3-{1-Benzenesulfonyl-3-[3,5-di-tert-butyl-2-(2,2-difluro-ethoxy)-phenyl]-1H-indol-5-yl}-but-2-enoic acid methyl ester (493 mg, 0.79 mmol) was dissolved in methanol (4 mL)/dioxane (8 mL) and treated with 1N NaOH (5.5 mL) at 60° C. for 4 h. Diluted with 1N HCl (25 mL) and extracted with ethyl acetate (3×25 mL). The combined organic portions were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo to provide crude material. The material was purified using radial chromatography by elution with hexane/ethyl acetate gradient to provide 158 mg (43%) of a lightyellow solid. Mp. 135-145° C. 1H NMR (250 MHz, CDCl3): δ 8.40 (bs, 1H), 7.92 (s, 1H), 7.47 (m, 3H), 7.39 (m, 2H), 6.26 (d, J=1.1), 5.49 (tt, 1H, J=55.3, J=4.3), 3.69 (td, 2H, J=14.0, J=4.0), 2.68 (d, 3H, J=1.0), 1.50 (s, 9H), 1.37 (s, 9H). MS [EI−] 468 (M−H)+. Analytical (C28H33NO3): Calculated C, 71.62; H, 7.08; N, 2.98. Found: C, 69.95; H, 7.38; N, 2.70.

Provenance & Evidence