Reaktion #672439

Reaktionsgleichung

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

acetic anhydride

→

4-Oxo-3-(3-phenyl-propionylamino)-pentanoic acid methyl ester

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to ambient temperature
2. 2
   EinengenAfter concentrating the reaction mixture under reduced pressure, DI water
3. 3
   workup.ADDITIONwas added (100 mL)
4. 4
   SonstigeThe reaction mixture was partitioned between water and CH2Cl2
5. 5
   WaschenThe organic phase was washed with 1N HCl
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe material was used without further purification

Vorschrift

2-(3-Phenyl-propionylamino)-succinic acid 4-methyl ester (10 g, 36 mmol), pyridine (50 mL) and acetic anhydride (45 mL) were combined in a 500 mL flask. The reaction mixture was heated at 90° C. for 2 h and then cooled to ambient temperature. After concentrating the reaction mixture under reduced pressure, DI water was added (100 mL). (Potential exotherm!). The reaction mixture was partitioned between water and CH2Cl2. The organic phase was washed with 1N HCl and then dried (MgSO4), filtered and concentrated under reduced pressure. The material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.31-7.20 (m, 5H), 6.79 (br d, J=7.6 Hz, 1H), 4.72 (X of ABX, 1H), 3.65 (s, 3H), 3.01-2.93 (m, 3H), 2.71-2.62 (m, 3H), 2.11 (s, 3H); MS (EI) 278.1 (M+H).

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