Sodium Hydroxide → HCID 178482647, compound

Participants

Reaction Steps

To 17 (50 mg, 0.113 mmol) in EtOH (2.5 mL) was added 10% aq. NaOH (1.3 mL) and the reaction mixture was stirred at room temperature for 2 h then at 85° C. for 10 rain. It was cooled and poured onto water (3 mL) and extracted with ethyl acetate (4×5 mL). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give product 18 as a white solid (9.0 mg, 26%); 1H NMR (400 MHz, CDCl3+4 drops CD3OD) δ 2.97 (s, 6H), 6.83 (d, J=8.9 Hz, 2H), 7.27 (d, J=1.0 Hz, 1H), 7.50 (d, J=8.8 Hz, 2H), 7.63 (s, 1H), 7.67 (d, J=1.0 Hz, 1H), 8.24 (d, J=2.1 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H); MS (CI) m/z 304.1 (MH), 345.1 (M+MeCN).

Provenance & Evidence