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Synthesis of (S)-alpha-ethyl-2-oxi-1-pentazane acetamide

A synthetic process, aminobutyramide technology, applied in the direction of drug combination, neurological diseases, organic chemistry, etc., can solve the problems of unsuitable for industrial production, harsh reaction conditions, high cost of raw materials, etc., to achieve large-scale industrial production and simplify synthesis The effect of reaction steps and simplification of the degree of risk of operation

Inactive Publication Date: 2006-12-06
TIANJIN TAIPU PHARMA SCI & TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The advantage of the first synthetic route is that there are fewer types of raw materials, cheap price, and low cost; the disadvantage is that the yield is only 4.7%, the reaction steps are long, and the reaction is too complicated, which is not suitable for industrial production
The total yield in the literature of the second synthetic route is 8.7%. The first few steps of this method are all classical reactions, but the cost of raw materials is higher than that of the first method. At the same time, some corrosion-resistant reaction equipment is needed in the operation, and the reaction conditions are harsh.

Method used

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  • Synthesis of (S)-alpha-ethyl-2-oxi-1-pentazane acetamide
  • Synthesis of (S)-alpha-ethyl-2-oxi-1-pentazane acetamide
  • Synthesis of (S)-alpha-ethyl-2-oxi-1-pentazane acetamide

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Experimental program
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Effect test

Embodiment 1

[0025] Synthesis (II) of embodiment 1.α-amino-butyronitrile

[0026] In a 2L three-necked flask, add 63.7g (1.3mol) of sodium cyanide, 400ml of 20% ammonia water, and then add 78.7g (1.47mol) of ammonium chloride, and dissolve under stirring. 58g (1mol) of n-propionaldehyde solution was added dropwise, stirred at room temperature overnight, and extracted three times with 200ml of dichloromethane. Combine the organic extracts, add molecular sieves and dry. Concentration under reduced pressure gave about 60 g of crude α-amino-butyronitrile as a yellow oily liquid. Add hot ferrous sulfate solution to the aqueous solution, stir evenly to remove excess cyanide ions, and wash the used reaction flask, beaker and other containers with ferrous sulfate solution, and finally combine the waste water solution and pour it into the waste bucket.

Embodiment 2

[0027] Synthesis (II) of embodiment 2.α-amino-butyronitrile

[0028] Add 320g (6.2mol) of sodium cyanide, 402g (7.4mol) of ammonium chloride, and 2500ml of ammonia water into a 5L three-necked flask, stir until the solid dissolves, then add 290g (5mol) of propionaldehyde dropwise at room temperature, stir for 5 hours, and use dichloro Methane (2000ml) was extracted four times, the organic layers were combined, dried and the solvent was evaporated to obtain 416g of light yellow oil.

Embodiment 3

[0029] The preparation of embodiment 3.α-amino-butanamide hydrochloride (III)

[0030] 60 g (0.714 mol) of the crude α-amino-butyronitrile obtained in Example 1 was added to a three-necked flask, and 450 g (3.64 mol) of saturated hydrogen chloride isopropanol solution (30%) was added dropwise with stirring under ice cooling, and stirred overnight at room temperature. Raise the temperature to reflux, stir for 30 minutes, cool, and filter to obtain 70 g of light yellow crude product, mp 204°C. The crude product is added to a round-bottomed flask, 500ml of ethanol (95%) is added, heated to reflux, until fully dissolved, cooled, and white crystals are precipitated, filtered and dried to obtain 47.6g, mp222°C, content 99.3%, yield 40% (the first step , two-step combined calculation yield)

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Abstract

A process for preparing (S)-alpha-ethyl-2-oxy-1-pyrrolidine acetamide used as antiepileptic includes such steps as strecker reacting between n-propanal and sodium cyanide, hydrolyzing, splitting and cyclizing.

Description

technical field [0001] The invention relates to a preparation method of antiepileptic drugs, in particular to a synthesis process of (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide (levetiracetam). Background technique [0002] Antiepileptic drugs are a class of drugs used to prevent and treat paroxysmal and temporary brain dysfunction caused by epileptic seizures. Levetiracetam (Levetiracetam) is an antiepileptic drug developed by Belgian UCB company. Compared with the existing antiepileptic drugs, this product does not show the effect of inhibiting and excitatory neurotransmission. In addition, this product can selectively Protect localized and primary generalized epilepsy without affecting the metabolism of other antiepileptic drugs. [0003] The preparation method about levetiracetam has been reported in the literature. EP0165919B1 and CN1015541B have introduced (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide (levetiracetam) respectively. There are two main synthetic routes, one...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/36A61P25/08
Inventor 李毅亮赵倩鲍玉荣康健磊
Owner TIANJIN TAIPU PHARMA SCI & TECH DEV
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