196601-67-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-2-N-acetamido-3-methoxypropionic acid is used as a building block for the synthesis of biologically active molecules, particularly in the production of peptide-based drugs. Its ability to form stable amide bonds makes it a crucial component in the development of pharmaceuticals.
Used in Drug Delivery Systems:
In the pharmaceutical industry, (R)-2-N-acetamido-3-methoxypropionic acid is used as a component in the design of drug delivery systems. Its properties contribute to the enhancement of drug bioavailability and the overall effectiveness of therapeutic treatments.
Used in Chemical Synthesis:
(R)-2-N-acetamido-3-methoxypropionic acid is utilized as a valuable tool in chemical synthesis due to its capacity to form stable amide bonds, which are essential in creating a variety of compounds with potential applications in various fields.

Upstream product

• 98632-99-6 O-Methyl-N-acetyl-DL-serine 
• 152612-69-6 (R)-2-acetamido-3-hydroxypropionic acid 
• 77-78-1 dimethyl sulfate 
• 105500-34-3 (R)-2-acetamido-3-acetoxypropanoic acid 
• 333-27-7 methyl trifluoromethanesulfonate 
• 1620134-82-8 (R)-2-N-acetamido-3-methoxypropionate benzyl ester 
• 1620134-81-7 (R)-2-N-acetamido-3-hydroxypropionate benzyl ester 
• 108-24-7 acetic anhydride 
• 86118-11-8 D-o-methylserine 
• 105591-02-4 (Z)-2-acetylamino-3-methoxy-2-propenoic acid 
• 105591-01-3 (Z)-2-acetylamino-3-methoxy-2-propenoic acid methyl ester 
• 764603-71-6 C₆H₉NO₄ 
• 188663-05-0 4-[(dimethylamino)methylene]-2-methyl-5(4H)-oxazolone 
• 1318791-64-8 O-methyl-D-serine trifluoroacetate 

Downstream Products

• 175481-36-4 lacosamide 
• 1197982-80-1 (R)-2-acetamido-3-methoxy-N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)propanamide 
• 1197982-90-3 (R)-N-4'-((3''-fluoro)benzylamino)benzyl 2-acetamido-3-methoxypropionamide 
• 1206634-91-4 (R)-N-4-(3-hydroxypropyl)benzyl 2-acetamido-3-methoxypropionamide 

Relevant academic research and scientific papers

A synthesis scheme for preparing method

The invention provides a preparation method of lacosamide, which comprises following steps: (A) performing a reaction between D-serine and acetic anhydride to generate an intermediate product N,O-diacetyl-D-serine; (B) performing methylation to the N,O-diacetyl-D-serine to obtain N-acetyl-D-serine methyl ether; (C) carrying out a reaction to the N-acetyl-D-serine methyl ether with benzylamine to obtain (R)-2-acetamido-N-benzyl-3-methoxyl propionamide. The preparation method is short in reaction route, can avoid racemization, and is high in yield and purity of a reaction product.

Method for preparing Lacosamide by one-pot method

The invention discloses a method for preparing Lacosamide by a one-pot method. The method comprises the steps: subjecting D-serine and an acetylation reagent to a reaction in a manner of taking dichloromethane as a solvent, and adjusting the pH of a reacted substance to 12-13 by an organic base after the reaction ends; then, controlling the temperature to -5 to 0 DEG C, and adding methyl trifluoromethanesulfonate into the reacted substance for a reaction; and cooling a reacted substance to the temperature of -30 to -25 DEG C, adding a dehydrating agent and benzylamine into the reacted substance for a reaction, carrying out depressurized-concentration drying on material liquid after the reaction ends so as to obtain crude Lacosamide, and then, carrying out recrystallization, thereby obtaining pure Lacosamide. The preparation method is simple and easy in operation, and the prepared Lacosamide has the purity of 99.90% or more and the chiral purity of 99.90%.

METHOD FOR PREPARING LACOSAMIDE

The present invention provides a novel method for preparing lacosamide with high chiral purity from D-serine. The method of the present invention can obtain lacosamide with high chiral purity in a high yield through a simple and environmentally-friendly process and thus can be easily applied to mass production.

A Method for preparing Lacosamide

In the present invention, provided is a novel method of manufacturing lacosamide with high purity of chiral from D-serine, which is allowed to obtain lacosamide with high purity of chiral in high yield through a simple, eco-friendly process and is accordingly used in mass-production.COPYRIGHT KIPO 2015

Total synthesis of lacosamide

Total synthesis of anticonvulsant amino acid, lacosamide, is reported. The key step is stereospecific allyl cyanate-to-isocyanate rearrangement, which proceeds with chirality transfer. The enantiopure starting material for the rearrangement step was accessed from ethyl l-lactate.

Substituted N -(biphenyl-4′-yl)methyl (R)-2-acetamido-3- methoxypropionamides: Potent anticonvulsants that affect frequency (Use) dependence and slow inactivation of sodium channels

We prepared 13 derivatives of N-(biphenyl-4′-yl)methyl (R)-2-acetamido-3-methoxypropionamide that differed in type and placement of a R-substituent in the terminal aryl unit. We demonstrated that the R-substituent impacted the compound's whole animal and cellular pharmacological activities. In rodents, select compounds exhibited excellent anticonvulsant activities and protective indices (PI = TD50/ED50) that compared favorably with clinical antiseizure drugs. Compounds with a polar, aprotic R-substituent potently promoted Na+ channel slow inactivation and displayed frequency (use) inhibition of Na+ currents at low micromolar concentrations. The possible advantage of affecting these two pathways to decrease neurological hyperexcitability is discussed.

PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES

The present invention relates to a process of manufacture of compounds of formula (B) wherein R1, R2 and R3 are as defined for compounds of formula (A), which process comprises hydrogenation of compounds of general formula (A). In particular, the present invention relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (B1), which is useful as an anticonvulsive drug.

PROCESS FOR THE PREPARATION OF LACOSAMIDE

Present invention relates to an improved and commercial process for the preparation of lacosamide ((R)-2-acetami-do-N-benzyl-3-methoxypropanamide) of formula (I). Present process utilizes high purity crystalline solids of formulae (XXXII) and (XIII) as key intermediates. Lacosamide is indicated for the adjunctive treatment of partial onset seizures in patients aged at least 17 years.

PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES

The present invention relates to a process of manufacture of compounds of formula (B) wherein R1, R2 and R3 are as defined for compounds of formula (A), which process comprises hydrogenation of compounds of general formula (A). In particular, the present invention relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (B1), which is useful as an anticonvulsive drug.

Process for the preparation of Lacosamide including resolution of O-methyl-DL-serine

The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.