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

Description

Desmethyl Lacosamide is a derivative of Lacosamide, which is a medication developed as an adjunctive treatment for partial-onset seizures and diabetic neuropathic pain. It is a potent anticonvulsant and exists as a white solid.

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

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• 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).