Hydrochloric Acid → HCID 68766221, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of PRC200.HCl (100 mg, 0.361 mmol) dissolved in 2 mL of MeOH was added 36% aq. formaldehyde solution (0.5 mL). This solution was heated at 65° C. overnight. After rotary evaporation of the volatiles, the product was leached with diethyl ether and hexane. The crude product could be purified by converting it to a hydrochloride salt, then crystallization from a solvent mixture prepared by dissolving 5 mL of MeOH, 20 mL of diethyl ether, and 17 mL of hexane. Yield 99 mg, 95%. 1H NMR (CD3OD) δ 7.82-7.69 (m, 4H), 7.63 (s, 1H), 7.48-7.39 (m, 2H), 7.23 (d, J=8.1 Hz, 1H), 7.15 (s, 4H), 5.29 (d, J=9.1 Hz, 1H), 5.09 (d, J=10.3 Hz, 1H), 5.02 (d, J=9.2 Hz, 1H), 3.87 (dd, J=12.2, 12.2 Hz, 1H), 3.75 (dd, J=13.0, 4.1 Hz, 1H), 3.71 (dd, J=4.1 Hz, 1H), 3.57-3.45 (m, 1H); MS: m/z (ESI) 290.11 (M+1)+; [α]D20 +125 (c 0.22, 9:1 EtOH:H2O).

Provenance & Evidence