Sodium Hydroxide → HCID 178525989, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl-4-(1,5-dibenzyl-1,4-dihydro-4-oxopyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 15, (0.080 g, 0.19 mmol) and 1 N NaOH (4 mL) in THF (12 mL) was stirred at 0° C. for 4 h. THF was distilled off and the residue acidified with 1 N HCl and extracted with EtOAc (2×25 mL), washed with brine solution (1×25 mL), dried over anhydrous Na2SO4 and EtOAc distilled off to give a yellow solid. The crude solid was triturated with diethylether, filtered and dried under vacuum. Finally the solid was triturated with chloroform, filtered and dried under vacuum for 24 h. Yield 0.065 g (84%), yellow solid, mp 140-142° C. 1H NMR (CDCl3+MeOH-d4, 500 MHz): δ 3.80 (s, 2H, CH2), 4.97 (s, 2H, CH2), 6.95 (t, 1H, CH, J=1 Hz), 7.13-7.40 (m, 11H, Ar—H and olefenic CH), 8.36 (d, 1H, CH, J=2.5 Hz). 13C NMR (CDCl3, 125 MHz): δ 33.4, 61.2, 120.5, 126.5, 127.5, 127.6, 128.6, 128.7, 128.7, 129.1, 129.1, 129.2, 129.2, 129.2, 129.4, 133.8, 135.9, 137.2, 138.2, 143.8, 163.8, 175.4. HRMS (M+H)+ calcd for C23H20NO5 390.1341, found 390.1343.

Provenance & Evidence