175481-37-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Acetamido-N-benzyl-3-methoxypropanamide is used as an active pharmaceutical ingredient (API) for the development of new medications. Its unique molecular structure allows it to interact with specific biological targets, making it a promising candidate for the treatment of various medical conditions.
Used in Chemical Research:
In the field of chemical research, (S)-2-Acetamido-N-benzyl-3-methoxypropanamide serves as a valuable compound for studying its chemical properties, reactivity, and potential applications in the synthesis of other complex molecules.
Used in Drug Synthesis:
(S)-2-Acetamido-N-benzyl-3-methoxypropanamide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it an essential building block for the development of new drugs with improved efficacy and safety profiles.
Used in Material Science:
The compound may also find applications in material science, where its specific chemical properties can be utilized to develop new materials with unique properties, such as improved mechanical strength, thermal stability, or chemical resistance.

Upstream product

• 58685-35-1 α-acetamido-N-benzyl-α-cyanoacetamide 
• 100-46-9 benzylamine 
• 75-36-5 acetyl chloride 
• 474534-78-6 (S)-N-benzyl-2-amino-3-methoxypropionamide 
• 152612-69-6 (R)-2-acetamido-3-hydroxypropionic acid 
• 108-24-7 acetic anhydride 
• 196601-69-1 (R)-2-amino-N-benzyl-3-methoxypropanamide 
• 77-78-1 dimethyl sulfate 
• 175481-38-6 Desmethyllacosamide 
• 1239016-92-2 (R)-N-benzyl 2-acetamido-3-(benzyloxy)propionamide 
• 1282623-41-9 O-tert-butyl-N-Z-D-serine benzylamide 
• 1282623-42-0 O-tert-butyl-D-serine benzylamide 
• 1084734-33-7 (R)-2-acetamido-N-benzyl-3-tert-butoxypropionamide 
• 1282623-44-2 O-benzyl-D-serine benzylamide 

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 academic research and scientific papers

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.

Synthetic route of lacosamide

The invention discloses a new synthesis route of lacosamide. The new synthesis route comprises the following steps: taking glycine ethyl ester hydrochloride as an initial raw material to react with methylbenzene, benzophenone and p-toluenesulfonic acid to obtain a compound of formula M1; reacting the compound of formula M1 with Xmethyl methyl ether to generate a compound of formula M2; reacting the compound of formula M2 with benzylamine under the catalytic action of sodium ethoxide to generate a compound of formula M3; reacting the compound of formula M3 under the action of acid to generate acompound of formula M4; reacting the compound of formula M4 with Ltartaric acid to generate a compound of formula M5; and enabling the compound of formula M5 to react with acetic anhydride to generate the lacosamide compound. The synthesis route has the advantages that the atom economy is high, the use of isopropyl chloroformate highly toxic products for preparing amide is avoided, the use of methylation reagents methyl iodide or dimethyl sulfate is avoided, the yield is high, and the like.

Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid

A catalytic enantioselective three-component Ugi reaction was developed. SPINOL-derived phosphoric acid with bulky 2,4,6-tricyclohexylphenyl groups at the 6,6′ positions was found to be the best catalyst to afford α-amino amide derivatives in good to excellent yields (62% to 99%) and enantiocontrol (81% to >99% enantiomeric excess). This asymmetric reaction was applicable well to an array of aliphatic aldehydes. The gram-scale synthesis, modification of dapsone, and enantioselective synthesis of (R)-Lacosamide underline the general utility of this methodology Influence of dihedral angles and substituents of the chiral phosphoric acids on the enantioselectivity was also discussed in this article.

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.

Preparation method of lacosamide

The invention provides a novel methylation method of a lacosamide synthesis intermediate, which comprises the following steps: methylating a compound I in a reaction solvent at a proper temperature byusing trimethyloxyonium tetrafluoroborate as a methylation reagent under alkaline condition to obtain a methylation product II. The reaction formula is shown in the specification. The method has theadvantages of mild reaction condition, simple post-treatment, green methylation reagent, no high toxicity and high reaction yield, and conforms to the safe and environment-friendly green chemical concept. The method is suitable for laboratory small-scale preparation and large-scale industrial production.

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)

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.

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE

The present invention relates to an improved process for the synthesis of (R)- Lacosamide in which free base of O-methyl-N-benzyl-D-Serinamide is not isolated before acylation. The process avoids the use of column chromatography and chiral resolution for the preparation of different stages of Lacosamide.

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.