Hydrochloric Acid → HCID 69601053, compound

Participants

Reaction Steps

To a solution of 3-8 (45 mg, 0.11 mmol) in 5.5 mL 2:2:1 THF:MeOH:water, at 0° C., was added lithium hydroxide (170 μL of a 2M solution in water) and the resulting solution was allowed to warm up to room temperature and stirred overnight. To the solution was added a 1M aqueous solution of HCl (1 mL) and the solution was extracted with ethyl acetate. The organic phases were then combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 50–100% ethyl acetate/hexanes to yield 37 mg of 3-9 as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.30–7.18 (m, 5H), 5.81 (dd, 1H), 5.53 (dd, 1H), 4.39 (q, 1H), 4.33 (q, 1H), 3.45 (dd, 1H), 3.33 (m, 1H), 2.97 (m, 2H), 2.77 (dd, 1H), 2.67 (m, 1H), 2.30 (t, 2H), 1.65–1.21 (m, 8H); MS (+ESI): m/z 378.2 (M+1)+.

Provenance & Evidence