4-Penten-1-OL → HCID 86683900, compound

Participants

Reaction Steps

N-(t-Butoxycarbonyl)alanine (3.1 g, 1 eq) and DCM (50 mL) were added to a vessel with stirring followed by the addition of CDI (3.1 g, 1.15 eq). The mixture was stirred at ambient temperature for 18 h after which time 4-penten-1-ol (1.8 g, 1.25 eq) was added. The mixture was stirred a further 18 h at ambient temperature at which point the reaction was quenched with 1N HCl. A biphasic mixture was formed and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 solution and then concentrated to give pent-4-en-1-yl 2-((tert-butoxycarbonyl)amino)propanoate as an oil. The oil was dissolved in DCM (50 mL) and methanesulfonic acid (2.2 g, 1.4 eq) was added. The mixture was stirred at ambient temperature for ˜22 h then cooled in an ice/water bath. Ethyl 2-chloro-2-oxoacetate (3.4 g, 1.5 eq) was added followed by drop-wise addition of triethylamine (5.0 g, 3 eq). The mixture was stirred for 7 h after which time the reaction was quenched by 1N HCl to form a biphasic mixture. The layers were separated and the organic layer was washed with a saturated aqueous NaHCO3 solution. The organic layer was then concentrated under reduced pressure to provide pent-4-en-1-yl 2-(2-ethoxy-2-oxoacetamido)propanoate as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (d, J=6.94 Hz, 1H), 5.66-5.83 (m, 1H), 4.90-5.05 (m, 2H), 4.49-4.62 (m, 1H), 4.31 (qd, J=7.17, 2.26 Hz, 2H), 4.13 (td, J=6.59, 2.13 Hz, 2H), 2.02-2.14 (m, 2H), 1.67-1.78 (m, 2H), 1.44 (d, J=7.19 Hz, 3H), 1.34 (t, J=7.15 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 171.64, 159.94, 155.83, 136.94, 115.40, 64.98, 63.10, 48.40, 29.71, 27.44, 17.88, 13.80; HRMS (M+Na) m/z, calcd for C12H19NO5Na, 280.1161; found, 280.1166.

Provenance & Evidence