Acetic Acid → HCID 74767505, compound

Participants

Reaction Steps

A solution of 13-1 (2.8 g, 5.6 mmol), acetic acid (0.41 ml, 7.2 mmol) and 1 N tetrabutylammonium fluoride (7.8 mL, 7.8 mmol) in THF (15.6 ml) was stirred at 23° C. for 16 h. Additional 1 N tetrabutylammonium fluoride in THF (4 mL, 4 mmol) was added and stirring was continued for 16 h. The white precipitate that formed was collected by filtration, washed with THF (2×50 mL) followed by ether (2×50 mL). The white solid was dissolved in DCM (100 mL) and washed with saturated aqueous sodium bicarbonate solution (2×100 mL), brine (2×100 mL) and water (2×100 mL) successively. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford a clear oil. The oil was triturated from 5:1 ether/EtOAc and the resulting white solid was collected by filtration and air dried to provide Example 13. 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H), 7.71-7.69 (m, 1H), 7.32-7.24 (m, 3H), 6.12 (d, 1H, J=5.4 Hz), 5.19-5.17 (m, 1H), 3.83 (s, 3H), 2.89-2.86 (m, 2H), 2.73 (s, 3H), 2.44 (s, 3H), 2.09-2.00 (m, 2H), 1.73 (d, 3H, J=6.6 Hz); MS: m/z=390.3 (M+H).

Provenance & Evidence