Desmethyl Lacosamide

Base Information

• Chemical Name: Desmethyl Lacosamide
• CAS No.: 175481-38-6
• Molecular Formula: C12H16N2O3
• Molecular Weight: 236.271
• European Community (EC) Number: 689-229-0
• UNII: PNH5357R26
• DSSTox Substance ID: DTXSID401248336
• ChEMBL ID: CHEMBL293954
• Mol file: 175481-38-6.mol

Synonyms:Desmethyl Lacosamide;175481-38-6;o-Desmethyl lacosamide;(R)-2-acetamido-N-benzyl-3-hydroxypropanamide;(R)-N-benzyl-2-acetamido-3-hydroxypropionamide;O-Desmethyl-lacosamide;(2R)-2-acetamido-N-benzyl-3-hydroxypropanamide;UNII-PNH5357R26;PNH5357R26;Propanamide, 2-(acetylamino)-3-hydroxy-N-(phenylmethyl)-, (2R)-;SCHEMBL47275;CHEMBL293954;LACOSAMIDE METABOLITE M1;N-benzyl-N2-acetyl-D-serinamide;CHEBI:173695;XRKSCJLQKGLSKU-LLVKDONJSA-N;DTXSID401248336;SPM 12809;AKOS030241147;CS-O-05957;LACOSAMIDE IMPURITY F [EP IMPURITY];(R)-2-acetamido-N-benzyl-3-hydroxy-propionamide;(R)-2-Acetamido-N-benzyl-3-hydroxypropionamide;Q27286652;(2R)-2-(Acetylamino)-3-hydroxy-N-(phenylmethyl)propanamide

Chemical Property of Desmethyl Lacosamide

Chemical Property:

• Vapor Pressure: 2.23E-14mmHg at 25°C
• Melting Point: 138-140°C
• PSA: 78.43000
• LogP: 0.58160
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 236.11609238
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

99%+, ^*data from raw suppliers

DesmethylLacosamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CO)C(=O)NCC1=CC=CC=C1
• Isomeric SMILES: CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1
• Uses: Lacosamide is a mediication developed as and adjunctive treatment of partial-onset seizures and diabetic neuropthic pain.Lacosamide is a potent anticonvulsant.

Technology Process of Desmethyl Lacosamide

There total 21 articles about Desmethyl Lacosamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(R)-N-benzyl 2-acetamido-3-(benzyloxy)propionamide (1239016-92-2) → Desmethyllacosamide (175481-38-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; for 2h; Product distribution / selectivity;

Reference yield: 93.0%

benzylamine (100-46-9) + (R)-methyl 2-acetamido-3-hydroxypropionate (288402-26-6) → Desmethyllacosamide (175481-38-6)

Guidance literature:

With triethylamine; at 0 - 20 ℃; for 12h; Reagent/catalyst; Temperature;

Reference yield: 92.5%

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate (1253790-58-7) + acetic anhydride (108-24-7) → Desmethyllacosamide (175481-38-6)

Guidance literature:

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate; With hydrogenchloride; In dichloromethane; water; at 20 ℃; for 1.5h;

acetic anhydride; With sodium hydroxide; In methanol; dichloromethane; water; for 1h; Product distribution / selectivity; Cooling with ice;

upstream raw materials:

acetic anhydride

(2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide

(R)-2-acetamido-3-hydroxypropionic acid

benzylamine

Downstream raw materials:

lacosamide

Refernces

• 1、 -. "Industrial preparation method of lacosamide". Paragraph 0018; 0023; 0024; 0028. . Retrieved 2018/03/26.
• 2、 -. "NOVEL PROCESS FOR THE PREPARATION OF (R)-N-BENZYL-2-ACETAMIDO-3-METHOXYPROPIONAMIDE". Paragraph 0046. . Retrieved 2014/11/11.