175481-38-6

Usage

Uses

Used in Pharmaceutical Industry:
Desmethyl Lacosamide is used as an adjunctive treatment for partial-onset seizures and diabetic neuropathic pain due to its potent anticonvulsant properties. It helps in managing and reducing the frequency of seizures and alleviates the pain associated with diabetic neuropathy.
Used in Research and Development:
Desmethyl Lacosamide is used as a research compound for studying its potential applications in various medical fields. Its anticonvulsant properties make it a valuable candidate for further investigation into its effectiveness in treating other neurological disorders and conditions.

InChI:InChI=1/C12H16N2O3/c1-9(16)14-11(8-15)12(17)13-7-10-5-3-2-4-6-10/h2-6,11,15H,7-8H2,1H3,(H,13,17)(H,14,16)/t11-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 175481-39-7 (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide 
• 100-46-9 benzylamine 
• 288402-26-6 (R)-methyl 2-acetamido-3-hydroxypropionate 
• 1322062-76-9 (R)-2-amino-N-benzyl-3-methoxypropionamide hydrochloride 
• 1253790-58-7 tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate 
• 1322062-75-8 (2R)-2-amino-N-benzyl-3-hydroxypropanamide hydrochloride 
• 1282623-44-2 O-benzyl-D-serine benzylamide 
• 1084734-33-7 (R)-2-acetamido-N-benzyl-3-tert-butoxypropionamide 
• 1282623-42-0 O-tert-butyl-D-serine benzylamide 
• 1282623-41-9 O-tert-butyl-N-Z-D-serine benzylamide 
• 1239016-92-2 (R)-N-benzyl 2-acetamido-3-(benzyloxy)propionamide 
• 219835-31-1 (R)-N-benzyl 2-N-(benzyloxycarbonyl)amino-3-hydroxypropionamide 
• 152612-69-6 (R)-2-acetamido-3-hydroxypropionic acid 

Downstream Products

• 175481-36-4 lacosamide 

Relevant academic research and scientific papers

Improved Synthesis and Impurity Identification of (R)-Lacosamide

An improved synthesis of Lacosamide 1 with high purity has been developed. Critical parameters of each step were identified as well as the impurities generated. Moreover, a creative method to improve chiral purity and stability of the key intermediate (R)-2-amino-N-benzyl-3-methoxypropionamide 10 by forming salt with an achiral acid (phosphoric acid) was discovered to ensure the chiral purity of (R)-Lacosamide. Phosphoric acid was further developed for the deprotection of the Boc group.

Industrial preparation method of lacosamide

The invention relates to an industrial preparation method of lacosamide. Esterification is performed on D-serine for generating D-serine methyl ester hydrochloride; the D-serine methyl ester hydrochloride reacts with acetyl chloride for generating N-acetyl-D-serine methyl ester; the N-acetyl-D-serine methyl ester reacts with benzylamine for obtaining (R)-2-acetamido-N-benzyl-3-hydroxypropionamide;the (R)-2-acetamido-N-benzyl-3-hydroxypropionamide reacts with methyl p-toluenesulfonate under an alkaline condition for obtaining (R)-2-acetamido-N-benzyl-3-methoxypropionamide. The preparation method provide by the invention has relatively mild reaction conditions in each steps; the raw materials are easy to obtain; no high-toxicity reagent is used; a safe and environment-friendly green chemistry idea is met; and the method is suitable for industrial amplification.

Process for the preparation of lacosamide

A novel process for the preparation of (R)-2-acetamido-N-benzyl-3-methoxypropionamide (Lacosamide) is described. It comprises reacting N-acetyl-D-serine methyl ester with benzylamine catalyzed by a non-nucleophilic base to obtain (R)-2-acetamido-2-N-benzyl-3-hydroxy propionamide followed by its methylation.

NOVEL PROCESS FOR THE PREPARATION OF (R)-N-BENZYL-2-ACETAMIDO-3-METHOXYPROPIONAMIDE

The invention is a novel process for the preparation of lacosamide by employing novel intermediates of formula III and IV:

PROCESS FOR THE PREPARATION OF LACOSAMIDE

The present invention relates to an improved process for the preparation of Lacosamide of Formula (I), comprising: O-methylating a compound of Formula (V) or a compound of Formula (XX) or a compound of Formula XXII; in the presence of a methylating agent and a base to produce Lacosamide of Formula (I).

Process for Producing Lacosamide

The present invention relates to a method for producing (R)-2-acetamido-N-benzyl-3-methoxypropionamide (lacosamide), by methylation of (R)-2-acetamino-2-N-benzyl-3-hydroxy-propionamide (V), in which the methylation is carried out at a temperature below 20° C.

Process for producing Lacosamide

Summary The present invention relates to a method for producing (R)-2-acetamido-N-benzyl-3-methoxypropionamide (lacosamide), by methylation of (R)-2-acetamino-2-N-benzyl-3-hydroxy-propionamide (V), in which the methylation is carried out at a temperature below 20 °C.

PROCESS FOR PREPARING (R)-2-ACETAMIDO-N-BENZYL-3-METHOXY-PROPIONAMIDE

Processes for preparing and purifying (R)-2-acetamido-N-benzyl-3-methoxy- propionamide of formula-1 and intermediates thereof are provided.

PREPARATION OF LACOSAMIDE

Processes for preparing lacosamide, for use in pharmaceutical compositions comprising lacosamide.

AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE

The present invention relates to an improved process for the preparation of Lacosamide of Formula (I), comprising: O-methylating a compound of Formula (V) or a compound of Formula (XX) or a compound of Formula XXII; in the presence of a methylating agent and a base to produce Lacosamide of Formula (I).