Acetone → HCID 10989578, compound

Participants

Reaction Conditions

Reaction Steps

Methyl L-aspartate (15.0 g, 0.082 mol), DI water (245 mL), acetone (20 mL), and Na2CO3 (30.8 g, 0.286 mol) were combined and cooled the solution to 5° C. 3-Phenyl-propionyl chloride (13.3 mL, 0.089 mol) was added dropwise via addition funnel over 10 min. The reaction was allowed to warm to ambient temperature and stir for 2 h. The reaction became very thick during this time. Added conc. HCl (50 mL) to the slurry until the pH was ≦4.0. The reaction mixture was extracted with CH2Cl2 (3×). The organic phase was washed with water and then dried (MgSO4), filtered and concentrated under reduced pressure. The clear, colorless oil was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.92 (br s, 1H), 7.28-7.17 (m, 5H), 6.57 (d, J=7.6 Hz, 1H), 4.87 (m, 1H), 3.67 (s, 3H), 2.96 (t, J=7.6 Hz, 2H), 2.89 (A of ABX, JAB=17.6 Hz, JAX=4.8 Hz, 1H), 2.88 (B of ABX, JBA=17.6 Hz, JBX=4.0 Hz, 1H), 2.69 (t, J=7.6 Hz, 2H); MS (EI+) 280 (M+H), 302 (M+H+Na).

Provenance & Evidence