175481-38-6

Basic information

• Product Name: Desmethyl Lacosamide
• Synonyms: Desmethyl Lacosamide;(2R)-2-(AcetylaMino)-3-hydroxy-N-(phenylMethyl)propanaMide;N-Acetyl-D-Serine Benzyl AMide
• CAS NO: 175481-38-6
• Molecular Formula: C₁₂H₁₆N₂O₃
• Molecular Weight: 236.26704
• Product Categories: Amino Acids & Derivatives;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 175481-38-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 581.8°C at 760 mmHg
• Flash Point: 305.7°C
• Appearance: /
• Density: 1.193g/cm³
• Vapor Pressure: 2.23E-14mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Desmethyl Lacosamide(CAS DataBase Reference)
• NIST Chemistry Reference: Desmethyl Lacosamide(175481-38-6)
• EPA Substance Registry System: Desmethyl Lacosamide(175481-38-6)

Safety Data

• Hazardous Substances Data: 175481-38-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Lacosamide is a mediication developed as and adjunctive treatment of partial-onset seizures and diabetic neuropthic pain.Lacosamide is a potent anticonvulsant.

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 
• 1322062-76-9 (R)-2-amino-N-benzyl-3-methoxypropionamide hydrochloride 
• 100-46-9 benzylamine 
• 288402-26-6 (R)-methyl 2-acetamido-3-hydroxypropionate 
• 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 
• 175481-39-7 (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide 

Downstream Products

• 175481-36-4 lacosamide 

Relevant articles and documents

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.

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.

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).