反应详情

温度

-20 °C

To a solution of (2R)-2-{[(benzyloxy)carbonyl]amino}pent-4-enoic acid (3a) (1.1 g) in DCM (5 mL) at −20° C. under N2 was added a mixture of EDAC.HCl (1.02 g) and DMAP (12 mg) in DCM (8 mL) portionwise. Methyl(1-phenylprop-2-en-1-yl)amine (1d) (650 mg) in DCM (3 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1.5 h at −20° C. and 4 h at RT, then diluted with DCM (100 mL) and washed with 0.2 N HCl, saturated NaHCO3, brine, dried (Na2SO4), filtered, and evaporated. The crude product was purified via flash chromatography (20% EtOAc/hexanes) to give the desired product as a viscous oil (1.04 g, 63%). 1H NMR (300 MHz, CDCl3) δ 2.38-2.47 (m, 1H), 2.50-2.59 (m, 1H), 2.66-2.82 (m, 3H-diastereomer/rotamer mixture), 4.77-4.80 (m, 1H), 5.08-5.17 (m, 4H), 5.22-5.48 (m, 2H), 5.69-5.82 (m, 2H), 6.03-6.14 (m, 1H), 6.39-6.43 (m, 1H), 7.25-7.35 (m, 10H). MS APCI, m/z=379 (M+1). LC/MS 2.72 min., Method A.

1. washwashed with 0.2 N HCl, saturated NaHCO3, brine
2. dry with materialdried (Na2SO4)
3. filtrationfiltered
4. customevaporated
5. customThe crude product was purified via flash chromatography (20% EtOAc/hexanes)