175481-37-5

Basic information

• Product Name: (S)-2-Acetamido-N-benzyl-3-methoxypropanamide
• Synonyms: (S)-2-Acetamido-N-benzyl-3-methoxypropanamide
• CAS NO: 175481-37-5
• Molecular Formula: C13H18N2O3
• Molecular Weight: 250.3
• EINECS: 200-158-5
• Product Categories: API
• Mol File: 175481-37-5.mol
• Article Data: 85

Chemical Properties

• Boiling Point: 536.447 °C at 760 mmHg
• Flash Point: 278.233 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0Pa at 25℃
• PKA: 14.19±0.46(Predicted)
• CAS DataBase Reference: (S)-2-Acetamido-N-benzyl-3-methoxypropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Acetamido-N-benzyl-3-methoxypropanamide(175481-37-5)
• EPA Substance Registry System: (S)-2-Acetamido-N-benzyl-3-methoxypropanamide(175481-37-5)

Safety Data

• Hazardous Substances Data: 175481-37-5(Hazardous Substances Data)

Usage

Uses

Epi-Lacosamide is an impurity of Lacosamide, a medication used for the adjunctive treatment of partial-onset seizures and diabetic neuropathic pain. Lacosamide is a potent anticonvulsant.

Upstream product

• 262845-82-9 N-Benzyl-2-Amino-3-Methoxypropionamide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 100-46-9 benzylamine 
• 118790-79-7 N-benzyl-2,3-dibromopropionamide 
• 1379592-20-7 (R,S)-N-benzyl-2-benzylamino-3-methoxypropionamide 
• 1379592-18-3 N-benzyl-2-azido-3-methoxy propionamide 
• 705283-58-5 N-benzyl-2-bromo-3-methoxypropionamide 
• 13304-62-6 N-benzylacrylamide 
• 108-21-4 Isopropyl acetate 
• 100-51-6 benzyl alcohol 
• 880468-89-3 tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate 
• 152612-69-6 (R)-2-acetamido-3-hydroxypropionic acid 
• 196601-68-0 (R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide 

Downstream Products

• 175481-36-4 (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide 
• 175481-36-4 lacosamide 
• 262845-82-9 N-Benzyl-2-Amino-3-Methoxypropionamide 
• 1318767-66-6 C₈H₇ClO₃*C₁₁H₁₆N₂O₂ 

Relevant articles and documents

Novel preparation method of lacosamide

The invention relates to a preparation method of high-purity lacosamide, and belongs to the technical field of organic synthesis. The technical problem to be solved by the invention is to provide a preparation method of lacosamide with mild reaction conditions and high optical purity. The preparation method comprises the following steps: carrying out condensation reaction on a carboxylic acid compound with a protecting group and benzylamine to generate an amide compound, carrying out deprotection under the condition of phosphoric acid, and introducing acetyl to prepare the lacosamide. The invention provides a novel industrial synthesis selection mode, the synthesis mode has the characteristics of simple process, mild reaction conditions, environmental friendliness and the like, can be used for preparing an optical high-purity target compound, and is beneficial to industrial production.

Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of N-Azidoacetyl Thioimides with Trimethyl Orthoformate: A New Combined Methodology for the Rapid Synthesis of Lacosamide and Derivatives

A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with trimethyl orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine is reported. The heterocyclic scaffold can be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides in high yields. Appropriate manipulation of the N-benzyl amide derivative provides an efficient access to the antiepileptic agent lacosamide through a new enantioselective C?C bond-forming process. DFT computational studies uncover clues for the understanding of the remarkable stereocontrol of the addition of a nickel(II) enolate to a putative oxocarbenium intermediate from trimethyl orthoformate.

Synthetic method of (by machine translation)

The synthesis method, takes ethyl acetoacetate as a starting material, as a starting raw material and reacts the compound of the formula II with trimethyl orthoformate to form the compound; of the formula III with the compound of the formula III under the action of a catalyst and a ligand H. 2 Of asymmetric hydrogenation to produce compound; of formula IV wherein the compound of formula IV is reacted with sodium azide in Schmidt rearrangement reaction to produce compound; of formula V in which compound of formula V is reacted with benzyl amine (BnNH under alkaline conditions of sodium methoxide. 2 ) The reaction scheme of the invention has the advantages. (: the economical efficiency of the atom is high, the use, of, the methyl tert-butyl carbonate is avoided, the use, of the methyl tert-butyl peroxyformate is avoided, yield is high, and the, like. (by machine translation)