Diethyl Ether → HCID 10781662, compound

Participants

Reaction Steps

Compound 15 (560 mg, 1.70 mmol) was stirred in a NaOH solution (2 N, 5 mL) at rt for 1.5 h, then diluted with water (20 mL) and neutralized with Dowex 50 w×8 (H+) resin. The mixture was filtered and washed with water and acetone. The combined filtrate was evaporated to dryness to give a pale-white solid, which was trituated with Et2O to give 16 as an off-white solid (450 mg, 84%): UV (MeOH) λmax 298.0,0 267.0 mn (sh); 1H NMR (CDCl3) δ 11.70 (s, 1H, NH, D2O exchangeable), 8.49 (s, 1H, H-6, j=8.1 Hz 7.22 (d, 1H, Ha, J=15.9 Hz), 6.73 (d, 1H, Hb, J=15.9 Hz), 5.89 (d, 1H, H-1′, J1′,F=16.8 Hz), 5.86 (d, 1H, 3′-OH, D2O exchangeable), 5.62 (bs, 1H, 5′-OH, D2O exchangeable), 5.05 (dd, 1H, H-2′, J2′,F=52.9 Hz), 4.18 (dm, 1H, H-3′, J3′,F=24.1 Hz), 3.89 (m, 3H, H-4′), 3.74 (m, 2H, H-5′).

Provenance & Evidence