Hydrochloric Acid → HCID 178525985, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl-4-(1,5-dibenzyl-1,2-dihydro-2-oxopyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 7 (0.069 g, 0.17 mmol) in MeOH (5 mL) at 0° C. was added a solution of 1N NaOH (0.5 mL) and reaction mixture allowed to stir at 0° C. for 30 min. Reaction was then allowed to stir at ambient temperature for 1 h. The reaction mixture was neutralized with 1 N HCl, the solid separated was filtered and dried under vacuum. Recrystallization with EtOAc/Hexane gave yellow solid. Yield 0.034 g (52%), yellow solid, mp 158-159° C. 1H NMR (CDCl3, 500 MHz): δ 3.82 (s, 2H, CH2), 5.26 (s, 2H, CH2), 7.16-7.39 (m, 10H, Ar—H), 7.45 (d, 1H, CH, J=2 Hz), 7.98 (s, 1H, olefenic CH), 8.26 (d, 1H, CH, J=2 Hz), 13C NMR (CDCl3, 125 MHz): δ 37.5, 53.3, 100.8, 119.8, 123.1, 127.0, 128.2, 128.5, 128.5, 128.6, 128.6, 128.9, 128.9, 129.0, 129.1, 129.1, 135.2, 138.4, 141.3, 145.1, 159.5, 162.3, 173.7; HRMS (M+H)+ calcd for C23H20NO5 390.1341, found 390.1342.

Provenance & Evidence