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Novel and efficient method for synthesis of amino acid

An amino acid and nitro acid technology, applied in chemical instruments and methods, preparation of organic compounds, medical preparations containing active ingredients, etc., can solve problems such as long processing procedures, difficulty in separating amino acids, and poor yields

Inactive Publication Date: 2011-06-29
GENERICS UK LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, the method yields the hydrochloride salt rather than the free base, and the practical difficulties of isolating amino acids from aqueous media are well known due to the formation of zwitterionic species
The formation of the HCl salt of racemic pregabalin (1) must be carried out under aqueous conditions, which leads to poor yields and lengthy workup procedures

Method used

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  • Novel and efficient method for synthesis of amino acid
  • Novel and efficient method for synthesis of amino acid
  • Novel and efficient method for synthesis of amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0154] 2-Hydroxy-4-methyl-1-nitro-pentane (4)

[0155] A mixture of tetrahydrofuran (1 vol, 1.0 L), nitromethane (2 eq, 1248 ml), and a catalytic amount of sodium methoxide (0.015 eq, 9.4 g) was stirred for 30 minutes to form a slurry of the nitromethane anion. The reaction mass was cooled in an ice-salt bath at 0°C and isovaleraldehyde (1 eq, 1 kg) was added in a controlled manner within 1 hour in such a way that the temperature did not rise above 5°C. After the last addition, the reaction mixture was stirred at 25-30°C for 6-8 hours. Completion of the reaction was verified by TLC.

[0156] Reduced pressure at 50°C (0.6kg / cm 2 ) to remove tetrahydrofuran. The obtained residue was cooled to 25-30 °C and quenched with water (4 vol, 4.0 L). The product was extracted with ethyl acetate (3 vol, 3.0 L) and isolated. The aqueous layer was further extracted with ethyl acetate (2.5 vol, 2.5 L) and the combined organic layers were washed with water (3 vol, 3.0 L). Ethyl acetate ...

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Abstract

The present invention relates to a novel process for the preparation of gamma-amino acids, such 5 as (+-)-3-(aminomethyl)-5-methyl-hexanoic acid (1), which is a key intermediate in the preparation of the potent anticonvulsant pregabalin, (S)-(+)-3-(aminomethyl)-5-methyl- hexanoic acid (2), and its analogues.

Description

technical field [0001] The present invention relates to a novel process for the preparation of γ-amino acids such as (±)-3-(aminomethyl)-5-methyl-hexanoic acid (1)) and their analogues, which are potent anticonvulsants Pregabalin (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid (2) is a key intermediate in the preparation. [0002] Background technique [0003] Synthesis, (±)-3-(aminomethyl)-5-methyl-hexanoic acid, or (±)-β-isobutyl-γ-amino-butyric acid, or (±)-3-(aminomethyl)-5-methyl-hexanoic acid, or (±) was first reported in 1989,953 )-isobutyl-GABA, hereinafter referred to as racemic pregabalin (1). The reported synthesis involved the addition of nitromethane to ethyl 2-enoate and reduction of the nitroester thus formed using palladium on carbon. The provided racemic pregabalin (1) is then hydrolyzed to the hydrochloride salt using hydrochloric acid. The free base of racemic pregabalin (1) was then prepared by ion exchange chromatography. [0004] An alternative me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/04C07C229/08C07C205/51A61K31/197A61P25/00C07C205/15
CPCC07C205/51C07C229/08C07C201/12C07C205/15C07C227/04A61P21/00A61P25/00A61P25/04A61P25/08A61P25/18A61P25/22A61P25/24A61P29/00A61P9/10C07C205/52
Inventor 维纳亚克·戈雷马赫什库马·加达卡尔达塔特雷亚·辛德
Owner GENERICS UK LTD