Hydrochloric Acid → HCID 10542456, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 13 (8.67 g, 26.2 mmol) in 260 mL of THF--CH3OH--H2O (3:1:1) was treated with LiOH--H2O (5.49 g, 131 mmol, 5 equiv) and the mixture was stirred at 25° C. for 25 h. The solution was acidified with the addition of 10% aqueous HCl (pH<1) and the product partially precipitated. The product was collected by filtration and the remaining aqueous phase was extracted with EtOAc (3×200 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford a combined 14 (7.94 g, 7.94 g theoretical, 100%): mp 235° C. (white powder, EtOH); 1H NMR (DMSO-d6, 400 MHz) δ8.73 (d, 1H, J=1.1 Hz), 8.34 (d, 1H, J=8.9 Hz), 8.32 (s, 1H), 7.88 (dd, 1H, J=1.5, 8.9 Hz), 7.63 (s, 1H), 7.57-7.34 (m, 5H), 5.38 (s, 2H); 13C NMR (CDCl3, 100 MHz) δ167.3, 153.8, 136.6, 135.5, 132.3, 130.3, 128.6, 128.3, 128.1, 127.6, 126.4, 123.4, 121.9, 118.8, 110.0, 107.5, 70.0; IR (KBr) vmax 3000 (br), 2227, 1687, 1577, 1499, 1419, 1343, 1283, 1250, 1105, 996, 915, 836, 740 cm-1 ; FABHRMS (NBA) m/z 304.0964 (M+ +H, C19H13NO3 requires 304.0974).

Provenance & Evidence