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Synthetizing method of lacosamide

A technology of lacosamide and synthesis method, which is applied in the synthesis field of lacosamide, can solve the problems of low total yield, complicated operation and high cost, and achieves the effects of improving conversion rate, reducing reaction steps and short reaction steps.

Inactive Publication Date: 2013-05-22
SUZHOU HONGRUI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such a synthetic scheme has long steps, high cost, cumbersome operation and low overall yield

Method used

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  • Synthetizing method of lacosamide
  • Synthetizing method of lacosamide
  • Synthetizing method of lacosamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Acylation reaction

[0024] Add 150ml of dichloromethane to the reaction flask, add 10.5g of D-serine under stirring, cool to 10-15°C, add 11.3ml of acetic anhydride dropwise, maintain this temperature for about 20 minutes, and raise the temperature to 25-30°C for 1 hour. After the reaction is over, add 50ml of water, separate the organic phase, and use 8%Na 2 CO 3 Wash with 50ml, then wash twice with 50ml water, combine the organic phases, evaporate the solvent, add 100ml diethyl ether to disperse and stir, and precipitate a white solid, filter, and dry to obtain 14.2g (R)-2-acetylamino-3-hydroxypropane Acid (II).

Embodiment 2

[0026] Acylation reaction

[0027] Add 150ml of chloroform to the reaction bottle, add 10.5g of D-serine while stirring, add 14.2ml of acetic anhydride dropwise after cooling to 10-15°C, maintain this temperature for about 30 minutes, and raise the temperature to 25-30°C to react for 1.5 hours. After the reaction is over, add 50ml of water, separate the organic phase, and use 8%Na 2 CO 3 Wash twice with 30ml of water, then twice with 50ml of water, combine the organic phases, evaporate the solvent, then add 100ml of diethyl ether to disperse and stir, a white solid is precipitated, filtered, and dried to obtain 13.9g of II.

Embodiment 3

[0029] condensation reaction

[0030] Add 150ml of dichloromethane to the reaction bottle, add II 10.3g under stirring, after dissolving, add dropwise the prepared solution of 15.6g of DCC dissolved in 60ml of dichloromethane, react at 25-30°C for 0.5 hours, add benzylamine 7.5 g, react at 25-30°C for 3 hours, spot the plate to judge whether the reaction is complete. After the reaction, filter, wash the filtrate 3 times with 50ml water, combine the organic layers, concentrate to dryness, add 20ml chloroform-80ml methyl tert-butyl ether mixed solvent for recrystallization, and obtain (R)-2-acetylamino-3- Hydroxy-N-benzylpropionamide (Ⅲ) 12.4 g.

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Abstract

The invention provides a synthetizing method of lacosamide. The method comprises the steps of: based on D-serine as a raw material, performing an acylation reaction with acetic anhydride and then performing a condensation reaction with benzylamine; and finally, performing a methylation reaction with dimethyl sulfate, thereby obtaining lacosamide, wherein N,N' dicyclohexylcarbodiimide (DCC) or N,N' carbonyl diimidazole (CDI) is used as a catalyst in the condensation reaction; and a phase transfer catalyst including triethyl benzyl ammonium chloride (TEBA), tetrabutylammonium chloride (TBAC), tetrabutylammonium bromide (TBAB) or tetrabutylammonium hydrogen sulfate (TBAHS) is adopted in the methylation reaction. The method has the advantages of being simple in synthetizing process, moderate in reaction condition, simple in after-treatment, high in yield and high in product purity.

Description

technical field [0001] The invention relates to a synthetic method of lacosamide, which belongs to the technical field of chemical pharmacy. Background technique [0002] Lacosamide, whose chemical name is (R)-2-acetamido-N-benzyl-3-methoxypropionamide, is a drug developed by Schwarz Pharma in Germany for the treatment of epilepsy and neuropathic pain. In September 2008, the European Union approved the marketing of Lacosamide Tablets of UCB Company in Belgium, which is used for adjuvant treatment of partial seizures in patients aged 16 and above with or without secondary grand mal seizures. In October 2008, the U.S. FDA approved lacosamide to be listed as an adjuvant drug in combination with other drugs for partial seizures of epilepsy. The trade name is Vimpat. Lacosamide is an anticonvulsant drug with a new dual mechanism of action, by selectively promoting the slow inactivation of sodium channels and regulating the collapse response mediator protein 22 (CRMP22), so as to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/22C07C231/12
Inventor 王德武
Owner SUZHOU HONGRUI MEDICAL TECH
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