Diethyl Ether → HCID 20607436, compound

Participants

Reaction Steps

A solution of the product 22A (170 mg, 0.459 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (96 mg, 0.505 mmol) and stirred for 5 minutes. Then ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. The residue was then dried under vacuum to provide 22 as a white hygroscopic solid. mp 45-47° C.; MS (ESI+) m/e 369 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 2.39 (s, 3H), 3.06 (s, 6H), 3.13 (m, 1H), 3.37 (dd, J=5, 14 Hz, 1H), 4.02 (m, 1H), 4.18 (dd, J=6, 12 Hz, 1H), 4.30 (dd, J=3, 12 Hz, 1H), 7.30-7.43 (m, 7H), 7.68(d, J=8 Hz, 2H), 7.71 (d, J=3 Hz, 1H), 8.01 (d, J=3 Hz, 1H); Analysis calculated for C16H18N2BrClO.1.15C7H8O3S.0.60H2O: C, 49.93; H, 4.95; N, 4.84; Found: C, 49.82; H, 4.88; N, 4.72; [α]25D=+58° (c=3.0, MeOH).

Provenance & Evidence