Reaktion #454206

Reaktionsgleichung

HCl

D-serine

benzylamine

→

N-Benzyl-2-aminohydracrylamide

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was heated
2. 2
   Temperaturat reflux (18 h)
3. 3
   Temperaturthe reaction mixture was heated for additional 18 h
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   Filtrationthe insoluble salts were filtered
6. 6
   Sonstigethe excess benzylamine was removed under high vacuum (Kugelrohr)
7. 7
   workup.DISSOLUTIONThe residue was dissolved in H2O (100 mL)
8. 8
   Extraktionthe product was extracted with CHCl3 (8×200 mL)
9. 9
   Trocknendried (Na2SO4)
10. 10
    Sonstigethe solvent was removed under reduced pressure
11. 11
    SonstigeThe residue was triturated with Et2O (150 mL)
12. 12
    Filtrationfiltered
13. 13
    Sonstige[α]23D (c=1, MeOH)=1.6°

Vorschrift

HCl (8.00 g, 219.4 mmol) was passed into MeOH (250 mL), and then D-serine ((R)-5) (20.00 g, 190.3 mmol) was added. The reaction solution was heated at reflux (18 h), then benzylamine (81.6 mL, 761 mmol) was added, and then the reaction mixture was heated for additional 18 h. The solvent was removed under reduced pressure, the insoluble salts were filtered, and the excess benzylamine was removed under high vacuum (Kugelrohr). The residue was dissolved in H2O (100 mL), and the product was extracted with CHCl3 (8×200 mL). The organic layers were combined and dried (Na2SO4), and the solvent was removed under reduced pressure. The residue was triturated with Et2O (150 mL) and filtered to vie 10.0 g (27%) of the product as white solid: mp 74-78° C.; [α]23D (c=1, MeOH)=1.6°.

Quelle