Acryloyl chloride → HCID 54755903, compound

Participants

Reaction Steps

A solution of tetrahydrofuran (20 mL), compound 22 (219 mg, 0.817 mmol) and diisoproylethylamine (156 μL, 0.895 mmol) was cooled to 0° C. Acryloyl chloride (67 μL, 0.828 mmol) was added and the reaction was allowed to proceed for 1 hour and afterwards concentrated in vacuo. The residue was dissolved in dichloromethane (20 mL) and washed with saturated sodium bicarbonate (20 mL). The aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (70 mg, 26% yield): 1H NMR (400 MHz, DMSO) δ 10.40 (s, 1H), 8.38 (s, 1H), 8.04 (s, 1H), 7.73 (d, J=8.0, 1H), 7.52 (t, J=7.9, 1H), 7.39 (d, J=7.7, 1H), 6.47 (dd, J=17.0, 10.1, 1H), 6.29 (dd, J=17.0, 2.0, 1H), 5.80 (dd, J=10.1, 2.0, 1H), 5.11 (hept, J=6.6, 1H), 1.51 (d, J=6.7, 6H); 13C NMR (100 MHz, DMSO) δ 163.47, 154.87, 151.90, 150.94, 144.73, 139.53, 132.54, 131.68, 129.88, 127.31, 123.42, 119.96, 119.22, 96.91, 48.80, 21.74; [M+H]+ calculated for C17H18N6O 323.1, found 323.5.

Provenance & Evidence