Amino-acid ester bromide type chiral ionic liquid and preparation method thereof

A technology of chiral ionic liquid and ester bromide salt, which is applied in the direction of organic chemical methods, cyanide reaction preparation, chemical instruments and methods, etc., can solve the problems of limited application range and rough preparation methods, and achieve low price and new development Variety, strong effect of stereoselectivity

Inactive Publication Date: 2015-11-18
海客迈斯生物科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, reports on the synthesis of ionic liquids using amino acids as chiral sources have gradually increased, such as CN1383920A, CN104693056A and CN1383921A respectively describing a kind of L-amino acid sulfate type chiral ionic liquid and its preparation method and L-amino acid sulfate type chiral ionic liquid. Amino acid ester cationic ionic liquid and its preparation method are

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Amino acid ester bromide salt type chiral ionic liquid, its structural formula is as follows:

[0023] , wherein, R is a variable group of α-amino acid, and said amino acid is D-, L-leucine, D-, L-lysine.

[0024] Among the amino acid cations mentioned, R ’ for CH 3 or CH 3 CH 2 .

Embodiment 2

[0026] Preparation method of amino acid ester bromide salt type chiral ionic liquid

[0027] 1. React amino acid with methanol and thionyl chloride at low temperature to obtain amino acid ester hydrochloride; mix amino acid with methanol and thionyl chloride at a ratio of 1:1.1:20 to 30 at -15°C In a low temperature environment of -10°C, slowly add thionyl chloride dropwise into methanol, continue to react for 2 hours after the drop is complete, warm up to room temperature, add amino acids in batches, keep stirring at 50°C for 3 hours, and then remove the solvent by rotary evaporation. Petroleum ether methanol recrystallization obtains the pure product of amino acid ester hydrochloride;

[0028] 2. Mannich reaction of amino acid ester hydrochloride, paraformaldehyde and acetone to obtain amino acid ester Mannich base; add paraformaldehyde to methanol, adjust pH to 5 with dilute hydrochloric acid, heat until paraformaldehyde dissolves , then drop to room temperature and add th...

Embodiment 3

[0032] Preparation of Chiral Ionic Liquid of Leucine Methyl Bromide Salt

[0033] (1) Synthesis of Leucine Methyl Ester

[0034] Take 125mL of methanol, add it to a 250mL three-necked flask, and cool it to -15°C in a low-temperature stirring reaction bath (the environment should be anhydrous during the reaction, and a drying tube should be connected to the branch pipe of the three-necked flask; the reaction will generate HCl and SO 2 Gas, use lye absorption device), then slowly add 10mL (0.138mol) freshly distilled SOCl 2 , control the reaction temperature below -10°C during the dropwise addition. After the dropwise addition is completed, continue to react at -10°C for 2 hours, rise to room temperature, add 16.5g (0.126mol) of leucine, and heat up to 50°C for 3 hours. , TLC to follow the reaction (using a 1:1 mixture of methanol and dichloromethane as a developing solvent, to prevent tailing, add a drop of diethylamine per milliliter), until the reaction reaches the end point...

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PUM

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Abstract

The invention discloses amino-acid ester bromide type chiral ionic liquid and a preparation method thereof. The general formula of the amino-acid ester bromide type chiral ionic liquid is A<+>Br<->, wherein A<+> is an amino-acid ester positive ion. The preparation method comprises the following steps: performing reaction on amino acid, methyl alcohol and thionyl chloride under low temperature to obtain amino-acid ester hydrochloride; performing mannich reaction on amino-acid ester hydrochloride, paraformaldehyde and acetone to obtain amino-acid ester mannich base; performing reaction on amino-acid ester mannich base and bromo-hydrocarbon to obtain the amino-acid ester chiral ionic liquid. The chiral amino-acid ester ionic liquid prepared through the preparation method disclosed by the invention has the advantages of high selectivity and chiral induction effect of a chiral substance, and non-volatilization, non-toxicity and no pollution of ionic liquid and is suitable for scale production of the fine chemical industry.

Description

technical field [0001] The invention relates to an amino acid ionic liquid and a preparation method thereof, in particular to an amino acid ester bromide salt-type chiral ionic liquid and a preparation method thereof, belonging to the technical field of chemical materials and their preparation. Background technique [0002] Ionic liquids are salts composed of organic cations and organic or inorganic anions that are liquid at or near room temperature. Ionic liquids have excellent physical and chemical properties such as low vapor pressure, good electrical conductivity, strong polarity, wide electrochemical window, high thermal stability, and good solubility and catalytic properties for certain substances. As well as the anion-cation structure that can be modified / tuned, and can be recycled, it is considered to be a new type of green solvent that can replace commonly used volatile organic solvents, and has been widely used in the field of chemical engineering. [0003] With t...

Claims

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Application Information

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IPC IPC(8): C07C229/12C07C227/18C07C229/26C07B53/00
Inventor 蔡明建
Owner 海客迈斯生物科技(上海)有限公司
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