Process for the preparation of lacosamide
AssigneeEuticals S.p.A.
InventorsAlberto Bologna, Patrizia Castoldi, Domenico Vergani, Giorgio Bertolini
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Abstract
A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-carcinogenic, such as methyl p-toluenesulfonate; the R enantiomer is isolated from the racemic mixture of Lacosamide after selective hydrolysis of the acetamide, salification of the racemic mixture with a chiral acid (HX*) in an organic solvent, resolution of the diastereoisomeric mixture, preferably by precipitation of the R enantiomer, and subsequent acetylation of the optically pure intermediate.
Claims49
A process for the synthesis of Lacosamide comprising the following steps:
- (a) hydroxymethylation of a compound of formula V
- to obtain a compound of formula VI
- (b) hydrolysis of the compound of formula VI to obtain a compound of formula VII
- (c) salification of the compound of formula VII with a chiral acid (HX*) in an organic solvent, to obtain a diastereoisomeric mixture VIII
- (d) resolution of the diastereoisomeric mixture VIII to obtain a salt IX
- (e) conversion of the salt IX into Lacosamide.
Dependencies are inferred from the claim text.