Hydrochloric Acid → Lacosamide EP Impurity E
Reaktionsgleichung
Cl.[NH2:2][C@@H:3]([C:6]([OH:8])=O)[CH2:4][OH:5].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[CH2:9]([NH:16][C:6](=[O:8])[CH:3]([NH2:2])[CH2:4][OH:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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°.