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Methof for preparing l-valine and d-valine by using chemical resolution process

A technology of D-valine and L-valine, which is applied in the field of preparation of chiral organic compounds, can solve problems such as no report on product optical purity and yield, cumbersome resolution process, insufficient product yield and optical purity, etc. problems, to achieve the effects of low production cost, simple synthesis process, and little environmental pollution

Inactive Publication Date: 2004-02-25
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of the chiral resolving agent used needs to be completed in four steps. The whole resolution process is relatively cumbersome, and the optical purity and yield of the product have not been reported.
In 1984, Tadashi Shiraiwa used HCl to adjust the pH value to 5.5 in an alkaline solution containing L-phenylalanine and DL-valine, and precipitated L-phenylalanine and D-valine adducts. After the compound is dissolved in water, L-phenylalanine is removed by active carbon adsorption to obtain D-valine, and its productive rate is 49-63%, and the optical purity is 84-100%, and the yield and optical purity of the product are not high enough

Method used

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  • Methof for preparing l-valine and d-valine by using chemical resolution process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve 2.34g of DL-Val in 20ml of dilute hydrochloric acid, heat to 80-100°C under stirring, add 3.58g of L-DBTA, react at this temperature for half an hour, then keep at 60°C for 1 hour, gradually a precipitate forms, and then Cool to about 15°C, filter with suction, dissolve the filter cake in 30ml of ethanol and 2 times the amount of triethylamine, stir for 1 hour, filter with suction, wash with ethanol, dry to obtain 0.94g of L-Val, and the resolution yield is 80.3% , [α] D 22 =+27.5°. Split and concentrate the mother liquor, adjust the pH value to 5.5 with alkali, stir, a white solid precipitates, filter with suction and wash with ethanol, dry to obtain 0.84g of D-Val, the yield is 71.8%, [α] D 22 =-27.5°.

Embodiment 2

[0035] Dissolve 2.34 g of DL-Val in 20ml of dilute hydrochloric acid, stir, heat to 90-100°C, add 3.76g of D-DBTA, react at this temperature for 50 minutes, then keep at 60°C for 1 hour, gradually a precipitate forms, and then cool to At about 15°C, filter with suction and wash with water, dissolve the filter cake in 30ml of ethanol and 2 times the amount of triethylamine, stir for 1 hour, filter with suction, wash with ethanol, dry to obtain 0.94g of D-Val, and the resolution yield is 80.3 %,[α] D 22 =-30°. Split and concentrate the mother liquor, adjust the pH value to 5.5 with alkali, stir, a white solid precipitates, filter with suction and wash with ethanol, dry to obtain 0.83g L-Val, yield 70.9%, [α] D 22 =+27.5°.

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Abstract

The present invention uses racemic valine (DL-Val) as raw material, uses inorganic acid as solvent, uses dextral dibenzoyl tartaric acid (D-DBTA) and levo-dibenoyl tartaric acid (L-DBTA0 as resolution agent according to the ratio of 1:0.5-1.2 in dilute inorganic solution, stirring for 0.5-2.0 hr. at 60-100 deg.C, then progressively cooling to room temp., filtering out crystal salt, using alkali to neutralize said crystal salt and mother liquor respectively in water and ethyl alcohol so as to respectively obtain the invented dextral valine (D-Val) and levo-valine (L-Val).

Description

1. Technical field [0001] The invention relates to a preparation technology of chiral organic compounds, in particular to a preparation method of L-valine and D-valine. 2. Background technology [0002] D-valine (L-Val) is an essential amino acid for nutrition, widely used as a food and feed additive, and also used in clinical amino acid infusion. L-Valine (D-Val) is an important chiral intermediate widely used in the synthesis of medicine and pesticide. For example, it can be used to synthesize antitumor drugs diaryl boron amino acid anhydride and diaryl boron aminoethyl ester compounds; it can also be used to synthesize new high-efficiency pesticides pyrethroids and halvalerate; its diiodophthaloyl derivatives The substance has antibacterial activity; the penicillamine derivatives of D-valine have the effect of enhancing immunity against AIDS and other diseases; its α-acyl cell wall dipeptide derivatives have the effect of enhancing the organism's resistance to pathogens ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/34C07C229/08
Inventor 蒋立建徐海青张征林未本美邹建忠
Owner SOUTHEAST UNIV
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