N-Carbethoxyphthalimide → HCID 11139382, compound

Participants

Reaction Steps

To a solution of L-2-amino-4-pentenoic acid (9.88 g) in an aqueous Na2CO3 (9.11 g, 150 mL) at RT was added N-carboethoxyphthalimide (18.8 g). The reaction mixture was stirred for 6 h at RT, gradually becoming homogeneous. The reaction mixture was transferred to a separatory funnel and extracted with DCM (3×). The basic aqueous layer was made acidic with 2N HCl and extracted with DCM (3×). The combined DCM layer was washed with brine, dried (Na2SO4), filtered and evaporated. The crude product was purified via column chromatography (2% MeOH/DCM) to give a viscous oil (20.0 g), which crystallized upon standing. 1H NMR (300 MHz, CDCl3) δ 2.93-3.11 (m, 2H), 4.97-5.11 (m, 3H), 5.65-5.79 (m, 1H), 7.71-7.75 (m, 2H), 7.83-7.88 (m, 2H). MS APCI-m/z=246 (M+1). LCMS 1.91 min., Method A.

Provenance & Evidence