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Microwave depsun method of photo-active amino acid or salt thereof

An optically active, amino acid technology, applied in the field of chiral compound separation, can solve the problems of difficult product separation and low racemization efficiency, and achieve the effects of uniform heating system, high racemization efficiency and low price

Inactive Publication Date: 2005-10-12
NINGBO ZHENHAI HAIDE BIOCHEM
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  • Summary
  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

The racemization efficiency of this method is not high, and product separation is difficult, so it is only suitable for analysis and laboratory-scale preparation
[0015] So far, using microwave heating technology under normal pressure conditions, using alkaline or acidic aqueous solution as the reaction solvent, adding a catalyst amount of aldehydes or ketones, or metal ions, or a mixture of aldehydes, ketones and metal ions Catalyst, rapid racemization of optically active amino acid or its salt method has not been reported in the literature

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Dissolve 16.5 grams (0.1mol) of L-phenylalanine in 200ml 2M aqueous solution of triethylamine, add 0.122 grams (0.001mol) of salicylaldehyde, mix well and put it in a microwave oven. The rated microwave frequency is 2450MHz, and the microwave output React for 40 minutes under the condition of power of 650W. Use 6M hydrochloric acid solution to adjust the pH of the reaction solution to the isoelectric point of phenylalanine to obtain 12.2 grams of D, L-phenylalanine as a precipitate, and then continue to concentrate the mother liquor to 1 / 5 of the original volume to obtain 2.48 grams of D, L-phenylalanine alanine. The total yield of the reaction is 88.96%, and the degree of racemization is 100%.

Embodiment 2

[0037] 17.8 grams (0.2mol) of partially racemic D-alanine were dissolved in 100ml of 2M potassium hydroxide methanol water mixed solution, and 1.21 grams (0.01mol) of anthranilaldehyde and 1.25 grams (0.01mol) of copper chloride were added, After mixing evenly, put it into a microwave oven, and react for 1.5h under the conditions of a rated microwave frequency of 915MHz and a microwave output power of 500W. 2M hydrochloric acid aqueous solution was added to the reaction solution to adjust the pH to 5, and the solution was diluted to 400ml. The solution was separated with 732 cationic resin to obtain 15.43 g of D,L-alanine. The total yield of the reaction is 86.67%, and the degree of racemization is 100%.

Embodiment 3

[0039] Dissolve 21.9 grams (0.1mol) of L-leucine sulfate in 200ml of 1M potassium carbonate aqueous solution, add 0.122 grams (0.001mol) of salicylaldehyde and 0.133 grams (0.001mol) of aluminum trichloride, mix well and put it in a microwave oven , reacted for 20 minutes under the condition of rated microwave frequency of 2450MHz and microwave output power of 100W. Use 6M hydrochloric acid solution to adjust the pH of the reaction solution to the isoelectric point of leucine, and obtain 7.21 grams of partially racemic L-leucine as a precipitate, and then continue to concentrate the mother liquor to 1 / 8 of the original volume to obtain 4.08 grams of partially racemic L-leucine. -Leucine. The total reaction yield is 86.18% (calculated as leucine), and the racemization degree is 65.2%.

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PUM

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Abstract

A microwave racemizing method for optical active amino acid or its salt. It is carried out by dissolving optical active amino acid or its salt into alkali or acid solution, adding aldehyde or ketone, or metal ion, or mixture of aldehyde, or ketone or metal ion as catalyst, racemizing reacting, and forming racemic amino acid or its salt. Its advantages include simple operation, high productivity, low cost, moderate reaction, and easy purification.

Description

1. Technical field [0001] The invention belongs to the technical field of separation of chiral compounds. Specifically, it relates to a preparation method of a chiral organic compound, especially a method for racemating D-type or L-type amino acids, which is also applicable to the racemization of other chiral amino compounds. 2. Technical background [0002] The unique internal heating method of microwave has the characteristics of high thermal efficiency, fast heating speed, uniform heating system, etc., and has been widely used in various fields of industrial and agricultural production and social life. In recent years, microwave heating technology has been introduced into the chemical reaction process, which can not only make the rate of organic reaction several times to thousands of times faster than traditional heating methods, but also has the characteristics of convenient operation, high yield and easy purification of products, and reflects environmental protection. ...

Claims

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Application Information

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IPC IPC(8): C07C227/36
Inventor 焦庆才刘毅郭丽芸李加友钱绍松贾晓娟
Owner NINGBO ZHENHAI HAIDE BIOCHEM
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