HCID 58000840, compound → HCID 178515783, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the intermediate from Example 1 Step C (11 g, 0.024 mol) in methanol (0.5 L) at 0° C. under nitrogen was added TiCl3 (15˜20%, 120 mL) over 45 minutes while maintaining the reaction temperature under 10° C. The solution was warmed to RT and stirred overnight. The volatiles were removed under reduced pressure, and the solution was made basic with saturated NaHCO3 and 5 N NaOH. Ethyl acetate was added and the mixture was stirred overnight. The solution was filtered through a Solka floe pad to remove the solids. The filtrate was extracted with EtOAc and the organic layer was then washed twice with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude residue which was purified by on silica gel (gradient elution with 2%-10% DCM-methanol as an eluant) to yield the title compound. 1H NMR (300 MHz, DMSO-d6): δ13.12 (m, 1H), 11.45 (br, 1H), 7.22˜7.70 (m, 9H), 6.10˜6.32 (m, 2H).

Provenance & Evidence