1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58691184, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-{[(benzyloxy)carbonyl]amino}pent-4-enoic acid (2a) (1.7 g) in DCM (8 mL) at −20° C. under N2 was added a mixture of EDAC.HCl (1.56 g) and DMAP (18 mg) in DCM (12 mL) portionwise. Methyl(1-phenylprop-2-en-1-yl)amine (1d) (1.0 g) in DCM (5 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at −20° C. and overnight 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 (1.8 g, 70%). 1H NMR (300 MHz, CDCl3) δ 2.41-2.47 (m, 1H), 2.52-2.57 (m, 1H), 2.66-2.82 (m, 3H-diastereomer/rotamer mixture), 4.77 (m, 1H), 5.11-5.17 (m, 4H), 5.22-5.41 (m, 2H), 5.68-5.82 (m, 2H), 6.08 (m, 1H), 6.39-6.41 (m, 1H), 7.26-7.35 (m, 10H). MS APCI, m/z=379 (M+1). LC/MS 2.99 min., Method A.

Provenance & Evidence