196601-67-9

Basic information

• Product Name: (R)-2-N-acetamido-3-methoxypropionic acid
• Synonyms: (R)-2-N-acetamido-3-methoxypropionic acid
• CAS NO: 196601-67-9
• Molecular Weight: 161.158
• Mol File: 196601-67-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 108-109 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 393.4±37.0 °C(Predicted)
• Density: 1.194±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-2-N-acetamido-3-methoxypropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-N-acetamido-3-methoxypropionic acid(196601-67-9)
• EPA Substance Registry System: (R)-2-N-acetamido-3-methoxypropionic acid(196601-67-9)

Safety Data

• Hazardous Substances Data: 196601-67-9(Hazardous Substances Data)

Usage

General Description

The chemical (R)-2-N-acetamido-3-methoxypropionic acid, also known as MAPA, is a compound used in the synthesis of biologically active molecules. It belongs to the class of organic compounds known as alpha amino acid esters and is a derivative of L-cysteine. MAPA is commonly used in the production of peptide-based drugs, as well as in the study and development of pharmaceuticals. It is known for its ability to form stable amide bonds, making it a valuable tool in chemical synthesis. MAPA has also been studied for its potential use in drug delivery systems and as a building block for the design of bioactive compounds.

Upstream product

• 67-56-1 methanol 
• 2104-89-4 D-serine methyl ester 
• 86852-11-1 diethoxyltriphenylphosphorane 
• 108-24-7 acetic anhydride 
• 152612-69-6 (R)-2-acetamido-3-hydroxypropionic acid 
• 77-78-1 dimethyl sulfate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 105500-34-3 (R)-2-acetamido-3-acetoxypropanoic acid 
• 1620134-82-8 (R)-2-N-acetamido-3-methoxypropionate benzyl ester 
• 1620134-81-7 (R)-2-N-acetamido-3-hydroxypropionate benzyl ester 
• 98632-99-6 O-Methyl-N-acetyl-DL-serine 
• 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 

Downstream Products

• 175481-36-4 lacosamide 
• 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 
• 1197982-80-1 (R)-2-acetamido-3-methoxy-N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)propanamide 

Relevant articles and documents

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%.

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.