Tetrahydrofuran → HCID 22137590, compound

Participants

Reaction Steps

The above solid (24) was taken up in saturated NaHCO3 (50 mL)/THF (50 mL). To this was added Fmoc-Osu (3.0 g, 9.0 mmol) at room temperature. The suspension became clear within 30 min. After stirring at room temperature overnight, the solution was concentrated to remove organic solvent, the resulting white suspension was acidified with 1 N HCl (50 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give a white solid (25) (3.63 g, >100%). 1H NMR (500 MHz, CDCL3) δ 7.77 (d, J=7.5 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H), 7.40 (t, J=7.5 Hz, 2H), 7.34 (dd, J=15.0, 11.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 2H), 6.21 (dd J=15.0, 11.0 Hz, 1H), 6.09 (dd, J=15.0, 7.0 Hz, 1H), 5.85 (d, J=15.5 Hz, 1H), 4.45 (br s, 2H), 4.18 (m, 3H), 2.83 (br s, 2H), 2.31 (m, 1H), 1.72 (m, 2H), 1.26 (m, 2H); MS (ES+) m/z 404.81 (M+H+).

Provenance & Evidence