Sodium Thiosulfate → 3-[(7-Fluoro-5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

Participants

Reaction Steps

A solution of 3-[(7-fluoro-5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (100 mg, 0.19 mmol) in acetonitrile (3 mL) was treated with trimethylsilyl iodide (0.138 mL) and stirred at RT under argon for 16 hours. Sodium thiosulphate solution (30 mL) was added and the mixture extracted with ethyl acetate (6×30 mL). The combined organic extracts were dried (MgSO4), filtered and evaporated to give a yellow oil. The oil was chromatographed on alumina, eluting with 0-50% methanol in DCM, to give the desired compound as an orange solid (19 mg). 1H NMR δ (CDCl3): 1.25 (d, 3H), 2.35-2.42 (m, 2H), 2.52 (s, 3H), 3.32-3.41 (m, 2H), 3.46-3.71 (m, 2H), 3.75 (d, 1H), 4.19-4.22 (m, 2H), 4.53-4.57 (m, 1H), 6.78 (d, 1H), 6.80 (t, 1H), 7.18 (s, 1H), 7.35 (s, 1H), 7.80 (d, 1H), 8.18 (s, 1H), 8.37 (s, 1H), 9.50 (s, 1H); m/z 518 (M+H)+, 516 (M−H)−

Provenance & Evidence