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Novel method for preparing levetiracetam midbody S-(+)-2-aminobutyrate hydrochlorate

A technology of aminobutyrate and aminobutyric acid, which is applied in the field of preparing levetiracetam intermediate S--2-aminobutyrate hydrochloride, can solve the problems of no literature reports, etc., and achieve simple steps and technical Parameters are easy to control the effect

Inactive Publication Date: 2009-07-29
SHAOXING STEPCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] It can be seen that the synthetic route of levetiracetam is still directly adopting (S)-α-amino acid as raw material or starting from 2-aminobutyric acid as raw material, converting into 2-aminobutyramide racemate and resolution The route of synthesis after (S)-α-aminobutyramide; use 2-aminobutyric acid, esterify it into 2-aminobutyrate, and then resolve it into (S)-α-aminobutyrate The method of the reaction has not been reported in the literature

Method used

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  • Novel method for preparing levetiracetam midbody S-(+)-2-aminobutyrate hydrochlorate
  • Novel method for preparing levetiracetam midbody S-(+)-2-aminobutyrate hydrochlorate
  • Novel method for preparing levetiracetam midbody S-(+)-2-aminobutyrate hydrochlorate

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Suspend 20.6 grams (0.2 moles) of 2-aminobutyric acid in 200 milliliters of ethanol, add 26 grams of thionyl chloride dropwise within 1 to 1.5 hours under stirring at 0 to 7 ° C to form a clear solution, stir at room temperature for about After 15 hours, the reaction solution was concentrated to dryness under reduced pressure, then ammonia water was added, and the oil layer was separated to obtain 25.5 g of ethyl DL-2-aminobutyrate with a yield of 97%.

[0036] In a 500 ml flask, add 13.1 g of ethyl 2-aminobutyrate and 25 ml of 95% ethanol. Heat to 80°C, add 6.7 g of L-malic acid, stir for 2 hours, filter, wash with an appropriate amount of 95% ethanol, the filter cake is S-(+)-2-aminobutyric acid methyl ester L malate solid. Add ethyl acetate to the solid of S-(+)-2-aminobutyric acid ethyl ester L-malate, feed ammonia gas for 2 hours, filter, wash with ethyl acetate, dry, and recover the solvent to obtain S-(+ )-2-aminobutyric acid ethyl ester 5.8 grams. Yield 44%, p...

Embodiment 2

[0040] Suspend 20.6 grams (0.2 moles) of 2-aminobutyric acid in 200 milliliters of ethanol, add 26 grams of thionyl chloride dropwise within 1 to 1.5 hours under stirring at 0 to 7 ° C to form a clear solution, stir at room temperature for about After 15 hours, the reaction solution was concentrated to dryness under reduced pressure, then ammonia water was added, and the oil layer was separated to obtain 25.5 g of ethyl DL-2-aminobutyrate with a yield of 97%.

[0041] In a 500 ml flask, add 13.1 g of ethyl 2-aminobutyrate and 25 ml of 95% ethanol. Heat to 35°C, add 6.7 g of L-malic acid, stir for 3 hours, filter, wash with an appropriate amount of 95% ethanol, the filter cake is S-(+)-2-aminobutyric acid methyl ester L malate solid. Add ethyl acetate to the solid of S-(+)-2-aminobutyric acid ethyl ester L-malate, feed ammonia gas for 3 hours, filter, wash with ethyl acetate, dry, and recover the solvent to obtain S-(+ )-2-aminobutyric acid ethyl ester 5.67 grams. Yield 43%, pu...

Embodiment 3

[0045] Under stirring at 0-7°C, 103 grams (1.0 mole) of 2-aminobutyric acid was put into 250 milliliters of methanol, and dry hydrogen chloride gas was introduced to saturation, and the reaction was stirred for about 20 hours, and the reaction solution was concentrated under reduced pressure, and then Ammonia water was added, and the oil layer was separated to obtain 111.2 g of DL-2-aminobutyric acid methyl ester with a yield of 95%.

[0046] In a 1 liter reaction flask, 105 g of methyl 2-aminobutyrate (0.9 mol) and 230 mL of methanol were added. Heat to 60°C, add 43 g of L-lactic acid, stir for 3 hours, filter, wash with an appropriate amount of methanol, and the filter cake is S-(+)-2-aminobutyric acid methyl ester L lactate solid. Add ethyl acetate to the solid of S-(+)-methyl 2-aminobutyrate L lactate, add an appropriate amount of solid sodium hydroxide, stir, separate the organic layer, dry, and recover the solvent to obtain S-(+) - Methyl 2-aminobutyrate 44 g. Yield 42...

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Abstract

The invention adopts a new method for optically resolving DL-2-amino-crotonic acid ester, thereby producing important intermediate S-(+)-2-amino-crotonic acid ester hydrochloride for preparing levetiracetam.

Description

technical field [0001] The present invention relates to a kind of method for preparing levetiracetam intermediate S-(+)-2-aminobutyrate hydrochloride, especially a kind of preparing levetiracetam intermediate S-( +)-2-Aminobutyrate hydrochloride new method. technical background [0002] Optically active amino acids and their derivatives, amino acid esters, amides, etc. are extremely important intermediates for the production of various physiologically active substances, such as drugs and pesticides. The chemical name S-(+)-2-aminobutyrate hydrochloride of compound of the present invention, structure is as follows: [0003] [0004] Levetiracetam is a drug developed by Belgian UCB company mainly for the treatment of localized and secondary generalized epilepsy. The US Food and Drug Administration (FDA) approved the drug in the US in April 2000. listed. [0005] There are generally two ways to prepare levetiracetam. One is the preparation by directly using optically act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/08C07C227/16C07C227/34
Inventor 齐陈泽沈永淼肖慧泉陈泳王新华
Owner SHAOXING STEPCHEM
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