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Production method of S-2-aminobutanamide

A technology of aminobutyramide and production method is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of optical isomers of carboxylic acid amides, etc., and achieves the effects of less investment in equipment, high safety, and reduced production costs

Inactive Publication Date: 2009-11-11
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There is no report on the direct conversion of other α-amino acids to prepare S-2-aminobutyramide

Method used

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  • Production method of S-2-aminobutanamide
  • Production method of S-2-aminobutanamide

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Experimental program
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Embodiment 1

[0030] 14.9 grams (100 mmoles) of L-(+)-methionine were dissolved in a mixed solvent of 250 milliliters of water and 70 milliliters of ethanol, the temperature was raised to 30-60° C., and 27.3 grams of ethyl 2-chloropropionate ( 200 mmol), after the addition, stir and react at the reaction temperature for 8 to 24 hours, then heat and reflux for 4 to 8 hours, cool to room temperature, add 100 ml of ethyl acetate to the system to extract once, wash twice , remove the solvent in the aqueous phase under reduced pressure, and filter to obtain a solid crude product, which is recrystallized in 350 mL of water-ketone-alcohol solvent to obtain pure white crystalline product S-2-amino-4-hydroxyl Butyrate hydrochloride 13.3 g (yield 85%), melting point 203 ° C, specific rotation -8.5 ° C (c = 2, H 2 O 22°C).

[0031] In an autoclave, dissolve S-2-amino-4-hydroxybutyrate hydrochloride (4.68 g, 30 mmol) in 30 ml of 33% HBr / AcOH solution, heat to 65-80 °C, and seal the reaction for 6 hou...

Embodiment 2

[0036]Dissolve 8.94 grams (60 mmol) of L-(+)-methionine in a mixed solvent of 200 milliliters of water and 30 milliliters of ethanol, raise the temperature to 30-60 °C, and add 6.5 grams of methyl dichloroacetate (60 milliliters) dropwise thereto. mol), after the addition, stir the reaction at the reaction temperature for 8 to 24 hours, then heat and reflux for 4 to 8 hours, cool to room temperature, add 60 milliliters of ethyl acetate to the system to extract once, wash twice, reduce The solvent in the aqueous phase was removed under pressure, filtered to obtain a solid crude product, and the obtained solid crude product was recrystallized in 200 mL of water-ketone-alcohol solvent to obtain a pure white crystalline product S-2-amino-4-hydroxybutyric acid Hydrochloride 7.58 grams, yield 81%, melting point 203 ° C, specific rotation -8.5 ° C (c = 2, H 2 O 22°C).

[0037] In an autoclave, dissolve S-2-amino-4-hydroxybutyrate hydrochloride (9.36 g, 60 mmol) in 50 ml of 30% HBr / A...

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Abstract

The invention discloses a production method of S-2-aminobutanamide, pertaining to the technical field of chemical synthesis. The production method comprises the steps of: adopting L-(+)-methionine as raw material, conducting demethylthiolation hydroxylation in the presence of alcoholic solvent or ether solvent through the action of organic carboxylate containing chlorine, forming S-2-amino-4-hydroxy butyrate hydrochloride, conducting hydroxy bromination to obtain S-2-amino-4-bromobutyric acid hydrobromide, conducting methyl esterification of carboxyl to obtain S-2-amino-4-bromo-methyl butyrate hydrochloride, conducting catalysis of nickel, hydrogenation and dehalogenation to convert the S-2-amino-4-bromo-methyl butyrate hydrochloride into S-2-amino methyl butyrate, and finally conducting ammonolysis to generate the S-2-aminobutanamide. The production method of S-2-aminobutanamide has the advantages of high yield and good safety.

Description

technical field [0001] The present invention relates to a process of preparing L-(+)-methionine as a raw material, through hydroxylation, demethylation, salt formation, hydroxyl bromination, carboxyl esterification, catalytic hydrogenation debromination and ester aminolysis reaction to prepare the antiepileptic drug levetra A new route to S-2-aminobutanamide, the main intermediate of racetam. technical background [0002] The chemical name S-2-aminobutanamide of compound of the present invention, structure is as follows: [0003] [0004] S-2-Aminobutyramide is the precursor and basic structural unit of important physiologically active substances, such as used in the synthesis of antiepileptic drug (S)-α-ethyl-2-oxotetrahydropyrrole acetamide (levatra racetam), a series of imidazolidinedione derivatives and intermediates for other complex chiral organic molecules. [0005] At present, the reported preparation methods of S-2-aminobutyramide include biological fermentatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/06C07C231/18C07C231/02
Inventor 齐陈泽曾敏峰沈永淼肖慧泉
Owner SHAOXING UNIVERSITY
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