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Chemical synthesis method of N-alcoxyloxalyl alanine ester

A kind of technology of alkoxy oxalylalanine ester and synthesis method, which is applied in chemical instruments and methods, organic chemistry, carboxylic acid amide preparation, etc., can solve the problems of harsh reaction conditions, low yield, difficult separation, etc., and achieve the goal of reaction The effect of mild conditions, advanced process route, and fast esterification speed

Active Publication Date: 2010-09-15
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method takes a long time to react, and uses a large amount of concentrated hydrochloric acid, the equipment is seriously corroded, and the operation is inconvenient
(2) Alanine ethyl ester and hydrochloric acid are salified, and then under the catalysis of triethylamine, react with oxalic diester to synthesize the target compound [Bull.Chem.Soc.Jpn, 1969, 1435]. This method is relatively expensive Ethyl alanine is used as a raw material, and the amount of triethylamine is large and the cost is high
(3) Under non-acidic conditions or in the presence of an organic base catalyst, alanine, oxalic acid, and oxalic diester react in an alcohol solution to prepare the target product. This method is easy to generate a by-product of alanine monoesterification, and is not easy to separate , the yield is not high [CN200480009214.X; WO2004087640]
The synthesis methods of other N-alkoxyoxalylalanine esters have more or less shortcomings such as low yield, troublesome operation, difficult separation and purification of products, and harsh reaction conditions. New methods for the synthesis of alanine esters are urgently needed

Method used

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  • Chemical synthesis method of N-alcoxyloxalyl alanine ester
  • Chemical synthesis method of N-alcoxyloxalyl alanine ester

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 89g (1mol) of alanine, 180g (2mol) of oxalic acid, and 460g of ethanol into a 2L four-neck flask equipped with a thermometer, a rectifying column, a water separator, a reflux condenser, and mechanical stirring, heat to dissolve, and add hydrogen sulfate Sodium 6g (0.05mol), with water agent toluene 200g, heated to reflux, rectified water for 40 hours. After the reaction is complete, add 50 mL of water, separate the water layer, dry the organic phase with 50 g of anhydrous sodium sulfate, evaporate the solvent at normal pressure until the internal temperature reaches 120 ° C, and recover the oxalyl diester under reduced pressure at 2 mmHg below 120 ° C to obtain light yellow Liquid N-ethoxyoxalylalanine ethyl ester 198.7g, gas chromatography detection content 95%, yield 87%, MS (EI): 217.3.

Embodiment 2

[0027] In a 2L four-neck flask equipped with a thermometer, rectifying column, water separator, reflux condenser and mechanical stirring, add 89g (1mol) of alanine, 180g (2mol) of oxalic acid, 600g of n-propanol, heat to dissolve, add 6 g (0.05 mol) of sodium bisulfate, 100 g of n-hexane with water agent, the temperature was raised to reflux, and the water was distilled for 40 hours. After the reaction is complete, add 50 mL of water, separate the water layer, dry the organic phase with 50 g of anhydrous sodium sulfate, evaporate the solvent at normal pressure until the internal temperature reaches 120 ° C, and recover the oxalyl diester under reduced pressure at 2 mmHg below 120 ° C to obtain light yellow Liquid n-propyl N-propoxyoxalylalanine 213.7g, content 94%, yield 82%, MS (EI): 245.2.

Embodiment 3

[0029] In a 2L four-neck flask equipped with a thermometer, rectifying column, water separator, reflux condenser and mechanical stirring, add 89g (1mol) of alanine, 180g (2mol) of oxalic acid, 740g of n-butanol, heat to dissolve, add Sodium bisulfate 6g (0.05mol), water-carrying benzene 200g, warm up to reflux, rectify water for 40 hours. After the reaction is completed, add 50 mL of water, separate the water layer, dry 50 g of the organic phase with anhydrous sodium sulfate, evaporate the solvent at normal pressure until the internal temperature reaches 120 ° C, and recover the oxalyl diester under reduced pressure at 2 mmHg below 120 ° C to obtain light yellow Liquid n-butyl N-butoxyoxalylalanine 246.9g, content 94%, yield 85%, MS (EI): 273.3.

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Abstract

The invention relates to a chemical synthesis method of N-alcoxyloxalyl alanine ester shown as a formula (I). The method comprises the following steps of: reacting alanine shown and oxalic acid which are shown as the formula (I) in alcohol of C1-C8 for 5-150 hours at 50-150 DEG C under the catalysis of bisulfate shown as a formula (II), wherein water generated in the reaction is timely evaporatedout with a water taking agent through a rectifying column and a water knockout drum; and after the reaction ends, carrying out after-treatment on reaction liquid to obtain the N-alcoxyloxalyl alanineester, wherein the mass ratio of the alanine to the oxalic acid to the bisulfate is 1:(1-10):(0.001-1), and the bisulfate is sodium bisulfate or potassium bisulfate or a mixture of the sodium bisulfate and the potassium bisulfate in arbitrary proportion. In the invention, since the bisulfate is used as a catalyst, and the method has high esterification speed, high reaction yield, low production cost, high catalyst activity, good selectivity, basically no monoesterification by-product, high product purity, easy separation and purification, moderate reaction condition and easy industrialization.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of N-alkoxy oxalyl alanine ester, in particular to a method for producing N-alkoxy oxalyl alanine ester with high yield. (2) Background technology [0002] N-Alkoxyoxalylalanine ester is widely used in medicine, pesticide and chemical industry, and has high practical value. For example, N-ethoxyoxalylalanine ethyl ester is a key intermediate of vitamin B6. [0003] Before the present invention was made, the chemical synthesis method of prior art N-alkoxy oxalyl alanine ester was to use alanine or alanine ester as raw material, through esterification or acylation synthesis target product, such as (1) Under the catalysis of concentrated hydrochloric acid, alanine, oxalic acid, oxalic acid diester, and ethanol are dehydrated and esterified by continuous distillation under the action of water-carrying agent benzene [China Pharmaceutical Industry Journal, 1994, 25 (9), 385; China Pharmaceutical Indust...

Claims

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Application Information

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IPC IPC(8): C07C231/14C07C233/47
Inventor 苏为科金灿施湘君章根宝
Owner ZHEJIANG UNIV OF TECH
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