Ammonium Chloride → HCID 90253453, compound

Participants

Reaction Conditions

Reaction Steps

N-[(4aR,6R,8aS)-6-(4-{[tert-Butyl(dimethyl)silyl]oxy}-1-hydroxybutyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C11) (28 mg, 47 μmol) was dissolved in tetrahydrofuran (0.3 mL) and cooled to 0° C. A solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 61 μL, 61 μmol) was added drop-wise, and the reaction mixture was allowed to warm to room temperature and then stir for 1 hour. After addition of saturated aqueous ammonium chloride solution, the mixture was extracted with ethyl acetate (3×5 mL); the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via chromatography on silica gel (Gradient: 35% to 100% ethyl acetate in heptane) provided the product as a white foam. Yield: 19 mg, 40 μmol, 85%. LCMS m/z 477.2 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.22 (br d, J=7.4 Hz, 2H), 7.49-7.56 (m, 1H), 7.42-7.49 (m, 2H), 7.39 (ddd, J=9.0, 9.0, 6.3 Hz, 1H), 6.85-6.97 (m, 2H), 4.16 (dd, J=12.1, 1.4 Hz, 1H), 3.85 (br d, J=12.1 Hz, 1H), 3.53-3.74 (m, 4H), 3.10-3.19 (m, 1H), 3.02 (dd, J=12.9, 4.1 Hz, 1H), 2.65 (dd, J=12.9, 2.5 Hz, 1H), 1.94-2.06 (m, 1H), 1.63-1.80 (m, 4H), 1.49-1.60 (m, 1H).

Provenance & Evidence