Reaktion #1268200

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 (3×100 mL)
3. 3
   WaschenThe combined organic layers were washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
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. The compound 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. Conc. HCl (50 mL) was added to the thick slurry until the pH was ≦4.0. The reaction mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with water, dried (MgSO4), filtered, and concentrated. 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).

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