Intermediate for producing lacosamide and a process for its preparation and conversion to lacosamide
The invention relates to ((R)-1-Benzylcarbamoyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester (compound III) with an ee of greater than 90%. and a process for producing the same.
1 . ((R)-1-Benzylcarbamoyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester having the chemical formula of compound III with an ee of greater than 90%
2 . ((R)-1-Benzylcarbamoyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester as claimed in claim 1 with an ee of greater than 97%.
3 . A process for producing (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide comprising methylating Compound III according to claim 1 to produce (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide with an enantiomeric excess greater than 90% with respect to the (R) enantiomer.
4 . The process according to claim 3 in which the ee of the (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide is greater than 97% with respect to the (R) enantiomer.
5 . A process for the production of lacosamide comprising treating (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide formed according to claim 3 to remove the tert-butoxy-carbonyl-protecting group to form an (R)-2-amino-N-benzyl-3-methoxypropionamide intermediate and acetylating the intermediate.
6 . A process for the production of lacosamide according to claim 5 in which (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide is converted to lacosamide without separation of an organic phase containing the (R)-2-amino-N-benzyl-3-methoxypropionamide intermediate prior to acetylation.
7 . A process according to claim 5 in which the lacosamide formed has an ee greater than 90%.
8 . A process according to claim 5 in which the lacosamide formed has an ee greater than 97%.
9 . A process according to claim 5 in which the lacosamide formed has an ee greater than 99%.