Pyridine → HCID 66685209, compound

Participants

Reaction Conditions

Reaction Steps

Pent-4-en-1-yl2-(2-ethoxy-2-oxoacetamido)-3-phenylpropanoate (0.80 g, 1 eq) and DCM (15 mL) were added to a vessel with stirring. Pyridine (0.23 g, 1.2 eq) was then added and the mixture was cooled to 15° C. Tf2O (1.0 g, 1.5 eq) was added to the mixture over 15 min and the mixture was warmed to ambient temperature. The solution was stirred for 3.5 h after which time the reaction was quenched by DCM and 20 wt % aqueous NaOAc to form a biphasic mixture. The layers were separated and the organic layer was extracted with 6N HCl (3×10 mL). The combined acid layers were washed with DCM and the pH was adjusted to ˜9 with solid K2CO3. The basic aqueous layer was extracted with DCM. The organic layer was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.74 (s, 1H), 7.10-7.35 (m, 5H), 4.43 (q, J=7.12 Hz, 2H), 4.22-4.29 (m, 2H), 4.21 (s, 2H), 2.78 (t, J=6.41 Hz, 2H), 1.93-2.06 (m, 2H), 1.41 (t, J=7.12 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 165.08, 152.25, 149.62, 138.86, 138.06, 129.62, 128.61, 127.80, 125.61, 125.23, 66.70, 60.97, 38.55, 23.93, 20.92, 14.10; HRMS (M+H) m/z, calcd for C18H20NO3, 298.1443; found 298.1450.

Provenance & Evidence