Reaktion #1812

Reaktionsgleichung

sarcosine benzyl ester

succinic anhydride

→

title compound

Ausbeute 86.3%

N-(3-Carboxypropanoyl)-N-methyl-glycine Benzyl Ester

Ausbeute 86.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 3 h
3. 3
   Temperaturcooled
4. 4
   Filtrationfiltered
5. 5
   Einengenthe filtrate was concentrated
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   Einengenwith concentrated hydrochloric
8. 8
   Extraktionextracted with ethyl acetate
9. 9
   WaschenThe organic phase was washed with water
10. 10
    Trocknendried (magnesium sulfate)
11. 11
    Einengenconcentrated

Vorschrift

A mixture of sarcosine benzyl ester (3.0 g, 30.7 mmol) and succinic anhydride (5.5 g, 30.7 mmol) in toluene (75 mL) was heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated. The residue was taken up in 5% aqueous sodium carbonate and extracted with ethyl acetate. The aqueous phase was adjusted to pH 3 with concentrated hydrochloric using Congo Red paper and extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate) and concentrated to yield the title compound (7.4 g, 67.5%): TLC Rf 0.48 (silica, 9:1:1 dichloromethane:methanol:formic acid).

Quelle