(Diethylamino)sulfur trifluoride → HCID 118235835, compound

Participants

Reaction Steps

DAST (0.04 mL, 0.34 mmol) was added to a solution of Example 173 (0.1 g, 0.23 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature under N2 gas. The mixture was stirred at room temperature for 2 h, quenched with water (5 mL) and poured onto saturated aqueous NaHCO3 solution (10 mL). The crude residue was extracted with EtOAc (3×10 mL), dried (MgSO4) and concentrated in vacuo. The resulting light yellow glass was purified by chromatography on silica (Biotage, 10 g cartridge), eluting with 0 to 100% EtOAc in heptanes. The resulting crude off white gum was further purified by preparative HPLC (preparative method C, neutral) to give the title compound (0.031 g, 31%) as a pale orange glass. δH (500 MHz, CDCl3) 8.80 (d, J 1.4 Hz, 2H), 7.79 (d, J 7.0 Hz, 1H), 7.37 (d, J 10.6 Hz, 1H), 7.30-7.27 (m, 1H), 7.17 (d, J 7.9 Hz, 1H), 7.11 (t, J 7.5 Hz, 1H), 6.90 (dd, J 7.7, 1.2 Hz, 1H), 6.62 (t, J 73.6 Hz, 1H), 4.29 (s, 2H), 2.52 (s, 3H), 1.83 (d, J 21.7 Hz, 6H). Method D HPLC-MS: MH+ m/z 445, RT 2.24 minutes.

Provenance & Evidence