Acetic Acid → HCID 71547234, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 42 (35 mg, 0.1 mmol) in methanol (0.5 mL) was added a solution of 2-ethylbutanal (20 mg, 0.2 mmol) in methanol (0.5 mL). To this solution was added acetic acid (30 μL, 0.5 mmol) followed by MP-cyanoborohydride resin (136 mg). The resulting mixture was shaken at 50° C. overnight and then filtered. The filtrate was concentrated. The residue was dissolved in 1:1 methanol:dimethyl sulfoxide and purified by HPLC (Gilson®, Xbridge™ 50×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/acetonitrile, UV=220 nm) to afford the title compound. 1H NMR (500 MHz, pyridine-d5/D2O) δ ppm 0.82 (t, 6 H, J=7.48 Hz), 1.24-1.36 (m, 4 H), 1.42-1.54 (m, 2 H), 1.83-1.91 (m, 1 H), 2.14-2.29 (m, 6 H), 2.36 (m, 1H), 2.84 (m, 2H), 2.93 (s, 1 H), 3.01 (m, 1H), 4.21 (m, 1H), 7.67 (t, 1H, J=8 Hz), 7.85 (d, 1H, J=8 Hz), 8.36 (d, 1H, J=8 Hz), 8.48 (s, 1 H), 10.02 (d, 1H, J=8 Hz); MS (ESI) m/z 434 (M+H)+.

Provenance & Evidence