Pyridine → HCID 66685727, compound

Participants

Reaction Conditions

Reaction Steps

Pent-4-en-1-yl2-(2-ethoxy-2-oxoacetamido)propanoate (1.05 g, 1 eq) and DCM (15 mL) were added to a vessel with stirring. Pyridine (0.39 g, 1.2 eq) was then added and the mixture was cooled to 15° C. Tf2O (1.7 g, 1.5 eq) was added to the mixture over 15 min and the mixture was warmed to ambient temperature to stir for 1.5 h. The reaction was quenched by the addition of DCM and 20 wt % aqueous NaOAc to form a biphasic mixture. The layers were separated and the organic layer was washed with water. The organic layer was then concentrated under reduced pressure to provide the title compound as yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.62 (s, 1H), 4.32 (q, J=7.12 Hz, 2H), 4.16-4.25 (m, 2H), 2.70 (t, J=6.44 Hz, 2H), 2.37 (s, 3H), 1.86-2.03 (m, 2H), 1.31 (t, J=7.12 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 165.15, 152.44, 147.98, 137.72, 128.73, 124.80, 66.85, 61.09, 23.98, 21.06, 18.98, 14.11; HRMS (M+H) m/z, calcd for C12H16NO3, 222.1130; found, 222.1133.

Provenance & Evidence