Hydrochloric Acid → HCID 59132793, compound

Participants

Reaction Steps

Compound 62.4 was dissolved in glacial acetic acid (1 mL) and water (0.3 mL) and heated to 95° C. for 16 h. 1N HCl (0.1 mL) was added and the reaction mixture was heated for another 16 h. The reaction mixture was poured into deionized water (50 mL) and extracted twice with diethyl ether. The combined organic layers were washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 5% methanol in dichloromethane eluant). Compound 62 was obtained as a thick oil (26 mg). LC-MS ESI (pos.) m/e: 468.1 (M+H). 1H NMR (500 MHz) (CDCl3) δ 8.14 (s, 1H); 7.70 (s, 4H); 7.66 (s, 1H); 7.56 (d, J=7.5 Hz, 1H); 7.50-7.45 (m, 2H); 7.22 (d, J=8.5 Hz, 2H); 6.96 (d, J=8.5, 2H); 5.99 (s, 1H); 5.12 (s, 2H); 4.67 (t, J=7.7 Hz, 1H); 4.08 (n, 2H); 3.16 (dd, J=16, 7.5 Hz, 1H); 2.95 (dd, J=16, 8.0 Hz, 1H); 1.17 (t, J=7.2 Hz, 3H).

Provenance & Evidence