175481-26-2

Basic information

• Product Name: LacosaMide (raceMate)
• Synonyms: LacosaMide (raceMate)
• CAS NO: 175481-26-2
• Molecular Formula: C₁₃H₁₈N₂O₃
• Molecular Weight: 250.29362
• Mol File: 175481-26-2.mol

Chemical Properties

• Boiling Point: 536.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.120±0.06 g/cm3(Predicted)
• Vapor Pressure: 0Pa at 25℃
• PKA: 14.19±0.46(Predicted)
• CAS DataBase Reference: LacosaMide (raceMate)(CAS DataBase Reference)
• NIST Chemistry Reference: LacosaMide (raceMate)(175481-26-2)
• EPA Substance Registry System: LacosaMide (raceMate)(175481-26-2)

Safety Data

• Hazardous Substances Data: 175481-26-2(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 175481-36-4 (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide 
• 98632-99-6 O-Methyl-N-acetyl-DL-serine 
• 108-24-7 acetic anhydride 
• 262845-82-9 N-Benzyl-2-Amino-3-Methoxypropionamide 
• 58685-35-1 α-acetamido-N-benzyl-α-cyanoacetamide 
• 171623-02-2 (R,S)-N-acetylserine-N-benzylamide 
• 74-88-4 methyl iodide 
• 55299-56-4 N-acetyl serine methyl ester 
• 80-48-8 methyl p-toluene sulfonate 
• 175481-29-5 methyl α-acetamido-N-benzylmalonamate 

Downstream Products

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

Relevant articles and documents

High-efficiency racemic lacosamide preparation method

The invention discloses a high-efficiency racemic lacosamide preparation method. The preparation method is characterized in that N-acetyl serine shown in a formula (II) is utilized as a raw material and completely reacts with methyl bromide under the action of sodium hydride to obtain 2-acetamido-3-methoxy methyl propionate shown in a formula (III), and then the 2-acetamido-3-methoxy methyl propionate generates ester exchange reaction with benzylamine under the catalyst of trifluoromethanesulfonate to obtain a product namely racemic lacosamide. The suspended lacosamide preparation method disclosed by the invention has an industrial process route which has the advantages of short reaction line, high yield, high atom utilization rate, simpleness in aftertreatment and low cost.

PROCESS FOR THE PREPARATION OF LACOSAMIDE

A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-car

PROCESS FOR THE SYNTHESIS OF LACOSAMIDE

A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-car

NOVEL PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES

The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).

Anticonvulsant enantiomeric amino acid derivatives

The present invention is directed to a compound in the R configuration about the asymmetric carbon in the following formula: STR1 pharmaceutical compositions containing same and the use thereof in treating CNS disorders in animals.

Synthesis and anticonvulsant activities of N-benzyl-2-acetamidopropionamide derivatives

Studies have demonstrated that 2-substituted N-benzyl-2-acetamidoacetamides (2) are potent anticonvulsants. A recent investigation has led to the hypothesis that an important structural feature in 2 for maximal anticonvulsant activity is the placement of a small, substituted heteroatom moiety one atom from the C(2) site. This paper validates this hypothesis. Twelve derivatives of N-benzyl-2-acetamidopropionamide have been prepared in which six different heteroatom substituents (chloro, bromo, iodo, oxygen, nitrogen, and sulfur) were incorporated at the C(3) site. Highly potent activities were observed for the two oxygen-substituted derivatives, N-benzyl-2-acetamido-3-methoxypropionamide (18) and N-benzyl-2-acetamido-3-ethoxypropionamide (19). The ED50 values in mice following intraperitoneal (ip) dosing for the maximal electroschock-induced seizure test for 18 and 19 were 8.3 and 17.3 mg/kg, respectively. These values compared favorably to the ED50 value found for phenytoin (ED50 = 6.5 mg/kg). Comparable activities were observed for 18 and 19 upon oral (po) administration to rats (18, ED50 = 3.9 mg/kg; 19, ED50 = 19 mg/kg; phenytoin, ED50 = 23 mg/kg). Evaluation of the individual stereoisomers for 18 demonstrated that the principal anticonvulsant activity resided in the (R)-stereoisomer. The ED50 value for (R)-18 was 4.5 mg/kg, and the ED50 for (S)-18 exceeded 100 mg/kg. This difference in activity for the two stereochemical isomers surpassed comparable values for other members within this class of compounds. The protective indices (PI = TD50/ED50) (where TD50 represents a neurotoxic dose impairing rotorod performance) for (R)-18 in mice (ip) and in rats (po) were 6.0 and > 130, respectively.