Chemical synthesis method of N-butoxyoxalyl amino acid butyl ester

A butyloxyoxalylamino acid butyl ester, chemical synthesis technology, applied in chemical instruments and methods, organic chemistry, carboxylic acid amide preparation, etc., to achieve the effects of simplifying the process, reducing corrosion, reducing equipment and raw materials

Inactive 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 process has a by-product N-butyl oxalyl amino acid monoester

Method used

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  • Chemical synthesis method of N-butoxyoxalyl amino acid butyl ester
  • Chemical synthesis method of N-butoxyoxalyl amino acid butyl ester
  • Chemical synthesis method of N-butoxyoxalyl amino acid butyl ester

Examples

Experimental program
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Effect test

Embodiment 1

[0023] In a 1000ml four-necked flask equipped with a thermometer, stirring, rectifying column, water separator, and condenser, add 38g of glycine, 63g of oxalic acid (containing 2 crystal waters), and 400ml of n-butanol, heat to dissolve, and the solution is clarified 100 g of dibutyl oxalate was added, and it was made to react at 100 degreeC (internal temperature) for 35 hours. During the heating, rectification, dehydration and esterification process of the reaction liquid, the water layer is continuously separated from the water trap at the top of the rectification column, and the n-butanol layer flows into the column. After the reaction was complete, the reaction solution was washed with water, and n-butanol and dibutyl oxalate were recovered by distillation under reduced pressure. The rest was butyl N-butoxyoxalylglycinate to obtain 112 g of light yellow oil with a yield of 87%. 1 HNMR: 7.1 (sbr, 1H), 4.13 (t, 2H), 4.10 (t, 2H), 3.76 (s, 2H), 1.55-1.57 (m, 4H), 1.29-1.32 (...

Embodiment 2

[0025] The molar ratio of feeding is glycine: oxalic acid: dibutyl oxalate is 1:3:3, and the input glycine is 19g. Other conditions and preparation steps are the same as in Example 1. 55 g of butyl N-butoxyoxalylglycine was obtained, and the yield was 85%.

Embodiment 3

[0027] Feeding molar ratio is glycine: oxalic acid: dibutyl oxalate is 1: 2: 1, the glycine 38g that drops in, other conditions preparation steps are with embodiment 1. Obtain N-butoxyoxalylglycine butyl ester 111g, yield is 86% .

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Abstract

The invention relates to a chemical synthesis method of N-butoxyoxalyl amino acid butyl ester. The synthesis method comprises the following steps of: reaching amino acid shown as a formula (II), oxalic acid shown as a formula (III) and dibutyl oxalate shown as a formula (IV) in n-butyl alcohol for 5-150 hours at 50-200 DEG C, wherein water generated in the reaction is removed through fine fraction in the reaction process; and then carrying out after-treatment on reaction liquid to obtain the N-butoxyoxalyl amino acid butyl ester shown as a formula (I), wherein the mass ratio of the amino acid to the oxalic acid to the dibutyl oxalate is 1:(1-10):(1-10); in the formula (I) and the formula (II), R is H and an alkyl group, a phenyl group, a benzyl group, a substituent phenyl group or a substituent benzyl group of C1-C6; and the substituent groups of the substituent phenyl group or the substituent benzyl group are respectively a methyl or a hydroxy. The invention has the advantages that a super acidic catalyst does not need to be used in the reaction process, and the reaction does not need to be carried out by steps, thereby simplifying the process and reducing equipment and raw materials; the corrosion to the equipment is reduced; and moreover, waste water polluting the environment cannot be generated in the production.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of N-butoxyoxalyl amino acid butyl ester, in particular to a method for synthesizing N-butoxy oxalyl amino acid butyl ester by a catalyst-free method. (2) Background technology [0002] In the synthesis of N-butoxyoxalyl amino acid butyl ester, the esterification of amino acid is generally realized under the catalysis of hydrochloric acid or hydrochloric acid-phosphoric acid, and then the oxalylation of amino group is realized in the presence of an acid removal agent. The process is complex, requires a lot of equipment, and requires high operation. At the same time, due to the use of highly corrosive hydrochloric acid, the equipment is seriously corroded, which obviously shortens the life of the equipment, and also produces salty wastewater, which affects the surrounding environment. [0003] CN86101512 discloses a method utilizing acidic conditions. Among them, amino acid reacts with oxalic aci...

Claims

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Application Information

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IPC IPC(8): C07C233/56C07C231/14C07C231/02
Inventor 苏为科金灿李杰施湘君章根宝
Owner ZHEJIANG UNIV OF TECH
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