Reaktion #672438

Reaktionsgleichung

HCl

Methyl L-aspartate

Na2CO3

acetone

3-Phenyl-propionyl chloride

→

2-(3-Phenyl-propionylamino)-succinic acid 4-methyl ester

Lösungsmittel

DI water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature
2. 2
   ExtraktionThe reaction mixture was extracted with CH2Cl2 (3×)
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe clear, colorless oil was used without further purification

Vorschrift

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).

Quelle