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Novel method for synthesizing lacosamide

A technology for synthesizing lacosamide and a new method, which is applied in the field of improved preparation of 2-acetamido-N-benzyl-3-methoxypropionamide, which can solve human health hazards, equipment corrosion, and a large amount of strong alkali and other issues to achieve the effect of high yield

Inactive Publication Date: 2011-11-23
SHANGHAI YICHENG MEDICAL TECH
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  • Abstract
  • Description
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Problems solved by technology

However, the use of highly toxic dimethyl sulfate as a methylation reagent not only has great harm to human health, but also requires a large amount of strong alkali in the reaction process, causing equipment corrosion and producing a large amount of waste salt

Method used

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  • Novel method for synthesizing lacosamide
  • Novel method for synthesizing lacosamide

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Embodiment Construction

[0017] A new method for the synthesis of lacosamide comprising O-methylation of compounds of formula I in a single step reaction

[0018] Formula I

[0019] The compound of formula II is obtained

[0020] Formula II

[0021] O-methylation in the present invention is achieved by adding dimethyl carbonate to N-protected serine and reacting at 0-10°C for 10-24 hours in the presence of an organometallic compound.

[0022] The organometallic compound of the present invention is preferably an organolithium compound; the organolithium compound is preferably an alkyllithium compound, such as butyllithium, methyllithium or aryllithium; the organolithium compound is more preferably tert-butyllithium or n-butyllithium, particularly preferably is n-butyllithium.

[0023] figure 1 As shown, the synthetic method of lacosamide according to this embodiment specifically includes the following steps:

[0024] (1) Preparation of (R)-2-N-Boc-amino-3-methoxypropionic acid using dimethyl c...

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Abstract

The invention discloses a novel method for synthesizing lacosamide. The novel method comprises that based on a one-step reaction, a compound shown in the formula I undergoes O-methylation to form a compound shown in the formula II, and the O-methylation is realized through a process that dimethyl carbonate is added into N-protective serine in the presence of an organometallic compound. The novel method adopts nontoxic and environmentally friendly dimethyl carbonate as a methylation reagent thus has no harm to human bodies and processing equipment and realizes a high yield.

Description

technical field [0001] The present invention relates to an improved process for the preparation of (R)-2-acetamido-N-benzyl-3-methoxypropionamide (lacosamide). Background technique [0002] (R)-2-Acetamido-N-benzyl-3-methoxypropionamide (recommended INN: lacosamide) is an anticonvulsant that can be used in the treatment of epilepsy and pain. US6048899 discloses two methods of preparing this compound. CN200580024175 discloses another method for synthesizing the compound. [0003] Method 2 of US6048899 involves formation of benzylamine followed by O-methylation. However, this method produces various impurities which must be removed by chromatography, which is not practical industrially. Moreover, the yield of a single step is only 80-85%. [0004] Method 1 of US6048899 involves O-methylation of N-protected D-serine followed by benzamide formation, N-deprotection and N-acetylation. Although this method has great improvement over method 1, it has great defects. Most import...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/12C07C231/02
Inventor 张俊杰
Owner SHANGHAI YICHENG MEDICAL TECH
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