Synthesis method of S-2-aminobutanamide hydrochloride

A technology of aminobutyramide and S-2-, which is applied in the field of organic chemical synthesis and preparation, can solve problems such as poor absorption of sulfur dioxide, hidden dangers of production safety, and increased production costs, and achieve low equipment requirements, increased yield, and mild method conditions Effect

Inactive Publication Date: 2013-04-03
江苏拜克新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires four-step reactions, and uses bromine as an environmentally unfriendly raw material. The amination process needs to be carried out under high pressure, which is not conducive to industrialization, while increasing production costs and bringing safety hazards to production; 2) using 2-amino Butyric acid is used as a raw material, and this product is obtained through chlorination, ammoniation, and acidification of thionyl chloride. This method uses thionyl chloride. Although the hydrogen chloride produced by thionyl chloride can be absorbed and discharged by lye, the absorption effect of sulfur dioxide Poor, sulfur-containing waste water is relatively polluting

Method used

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  • Synthesis method of S-2-aminobutanamide hydrochloride

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Embodiment 1

[0022] Into a 2000ml reaction bottle, add 1350g of methanolic ammonia solution containing 25% ammonia by weight, take a sample for inspection to ensure that the ammonia content is 25%, lower the temperature below 10°C, and add 300g of 2-bromine dropwise within 2 hours Methyl butyrate, after dripping methyl 2-bromobutyrate, close the reaction vessel, keep it warm for 1 hour, remove the freezer, raise the temperature naturally to 20°C, stir for 40 hours, during the heat preservation process, take a sample to detect methyl 2-bromobutyrate , when the content is less than 0.5%, reach the end of the reaction, evaporate to dryness under reduced pressure at 75°C to obtain a white solid, ammonia water can be recycled in this process, add 750g of anhydrous isopropanol to the obtained white solid, reflux for 2 hours, and then freeze To 10°C, shake filter, the white solid obtained by the shake filter is ammonium bromide for solid waste treatment, the mother liquor obtained by the shake fil...

Embodiment 2

[0026] Into a 2000ml reaction bottle, add 1350g of methanolic ammonia solution containing 25% ammonia by weight, take a sample for inspection to ensure that the ammonia content is 25%, lower the temperature below 10°C, and add 300g of 2-bromine dropwise within 3 hours Methyl butyrate, after dripping methyl 2-bromobutyrate, close the reaction vessel, keep it warm for 1 hour, remove the freezer, raise the temperature naturally to 20°C, stir for 38 hours, during the heat preservation process, take a sample to detect methyl 2-bromobutyrate , when the content is less than 0.5%, reach the end of the reaction, evaporate to dryness under reduced pressure at 60°C to obtain a white solid, ammonia water can be recycled in this process, add 800g of anhydrous isopropanol to the obtained white solid, reflux for 2 hours, and then freeze To 10°C, shake filter, the white solid obtained by the shake filter is ammonium bromide for solid waste treatment, the mother liquor obtained by the shake fil...

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Abstract

The invention discloses a synthesis method of S-2-aminobutanamide hydrochloride, which comprises the following steps of: 1) ammoniation: respectively carrying out ammoniation on methyl 2-bromobutyrate in a methanol-ammonia solution and anhydrous isopropyl alcohol so as to generate DL-2-aminobutanamide; 2) resolving: combining the DL-2-aminobutanamide with an L-tartaric acid to carry out salting-out, and carrying out resolution and purification on the obtained product; and 3) releasing and salifying: directly feeding hydrogen chloride into a crude product subjected to resolution and purification so as to carry out releasing and salifying, thereby obtaining S-2-aminobutanamide hydrochloride with optical activity. The method disclosed by the invention is cheap and easily obtained in raw materials, simple in operation, mild in conditions, high in process safety, low in equipment requirement, and easy to realize industrialized large-scale production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis and preparation, in particular to a method for synthesizing S-2-aminobutyramide hydrochloride. Background technique [0002] The chemical name of the chiral drug levetiracetam is (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide, and its preparation method has been reported in literature, such as CN1015541B, EP1566376 and CN1583721A. 2-aminobutyramide hydrochloride is an important intermediate of levetiracetam, and there are many patent documents such as WO2006 / 095362 and US2007 / 087924 that report the use of 2-aminobutanamide hydrochloride to synthesize levetiracetam Tan, so 2-aminobutyramide hydrochloride in levetiracetam. The main methods of chemically synthesizing 2-aminobutyramide hydrochloride are as follows: 1) Using butyric acid as a starting material, 2-aminobutyramide is obtained through bromination, methylation, ammoniation and acidification steps, and finally the acid is adjusted to ob...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/12C07C231/02
Inventor 陆孙彬周乔周士涛
Owner 江苏拜克新材料有限公司
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