(Diethylamino)sulfur trifluoride → HCID 90060353, compound

Participants

Reaction Steps

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-hydroxy-ethyl)-undec-4-enoate (157 mg, 0.211 mmol) was dissolved in tetrahydrofuran (5.0 mL), and (diethylamino)sulfur trifluoride (0.0360 mL, 0.273 mmol) was then added at room temperature. The mixture was stirred for 4 hours, then quenched with a saturated aqueous solution (15 mL) of sodium bicarbonate, and extracted with dichloromethane (15 mL). The organic layer was then dried over anhydrous sodium sulfate and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 71.1 mg (0.0953 mmol, 45% yield) of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(2-fluoro-ethyl)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate.

Provenance & Evidence