Acetic Acid → HCID 67443036, compound

Participants

Reaction Steps

To a stirred suspension of compound 271-A (80 mg, 0.188 mmol) and AcOH (12 μl, 0.207 mmol) in DCM (10 mL) was added 2,5,8,11-tetraoxamidecan-13-al (78 mg, 0.377 mmol, L. Gorini, et. al. SynLett., 2006, 948-950). After 30 min, sodium triacetoxyborohydride (120 mg, 0.565 mmol) was added and the reaction mixture was stirred at RT for 1 h. DMF (1 mL) and THF (2 mL) were added to the suspension that was stirred at RT for and additional 18 h. The reaction mixture was diluted with water and concentrated. The residue was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 15/85 over 20 CV) to afford a material that upon trituration with MTBE afforded an unexpected compound 277 (30 mg, 0.06 mmol, 32% yield) as beige solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.78 (s, 1H), 8.44 (d, J=5.2 Hz, 1H), 7.71 (dd, J=2.4 and 13.6 Hz, 1H), 7.47 (s, 1H), 7.33 (t, J=9.2 Hz, 1H), 7.22-7.15 (m, 1H), 6.63 (d, J=2.0 Hz, 1H), 6.55 (d, J=5.2 Hz, 1H), 6.37 (s, 1H), 3.40 (t, J=6.4 Hz, 1H), 3.14-3.09 (m, 2H), 2.68-2.50 (m, 5H), 2.40 (t, J=6.4 Hz, 2H), 1.56-1.41 (m, 4H), 0.68-0.61 (m, 2H), 0.44-0.40 (m, 2H). MS (m/z): 497.2 (M+H).

Provenance & Evidence