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Preparation process of amino acid N-carboxylic acid anhydride

A preparation process and amino acid technology, applied in the field of chemical synthesis and production, can solve problems such as hidden safety and environmental protection risks, and the synthesis method has not achieved major breakthroughs, and achieves low environmental pollution, simple and convenient post-processing operations, and low energy consumption in the production process. Effect

Inactive Publication Date: 2021-06-04
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] To sum up, it can be seen that the development of the synthesis method of NCA for many years has not made a major breakthrough, and the dangerous phosgene derivatives are still used, and the solvent in the reaction needs to be strictly dewatered, and the phosgene derivatives must also be dried. The cumbersome operation of removing water, especially in the post-treatment, still has unreacted phosgene derivatives decomposed to produce toxic substances, and there are still hidden dangers to safety and environmental protection in large-scale production, so the disadvantages of the existing production process are more obvious when the production scale is further expanded

Method used

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  • Preparation process of amino acid N-carboxylic acid anhydride
  • Preparation process of amino acid N-carboxylic acid anhydride
  • Preparation process of amino acid N-carboxylic acid anhydride

Examples

Experimental program
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Effect test

Embodiment 1

[0050] The synthesis of embodiment 1,4-isopropyl-2,5-oxazolidinedione:

[0051] The reaction process is as follows:

[0052] STEP1: Synthesis of N-(methoxycarbonyl)-L-valine

[0053] Take 1.17Kg (10mol) of L-valine, 5L of 2mol / L sodium hydroxide solution, and 1.06Kg (10mol) of sodium carbonate into a 20L reaction kettle, start stirring, and after the L-valine is completely dissolved, dissolve the solution The temperature dropped to -10°C, and 5L of 1,4-dioxane solution containing 1.89Kg (20mol) of methyl chloroformate was added dropwise. The temperature of the solution was kept below 20°C during the dropwise addition, and the reaction was carried out at 25°C for 8 hours after dropping. After the reaction is complete, the reaction solution is extracted with 2.5 L of ethyl acetate, the organic phase is discarded, the water phase is cooled to below 10°C, concentrated hydrochloric acid is added dropwise until the pH is 2, and then stirred at 10°C for 30 minutes, a large amount ...

Embodiment 2

[0056] Embodiment 2, the synthesis of 4-((1H-indol-3-yl)methyl)oxazolidine-2,5-dione:

[0057] The reaction process is as follows:

[0058]

[0059] STEP1: Synthesis of N-(methoxycarbonyl)-L-tryptophan

[0060] Take 2.04Kg (10mol) of L-tryptophan, 5L of 10% potassium hydroxide solution, and 1.38Kg (10mol) of potassium carbonate into a 20L reaction kettle, start stirring, and after the L-tryptophan is completely dissolved, lower the temperature of the solution Drop below -10°C, add dropwise 5L of a tetrahydrofuran solution containing 1.89Kg (20mol) of methyl chloroformate, keep the temperature of the solution below 20°C during the dropwise addition, and react at 40°C for 12 hours after dropping. After the reaction is complete, the reaction solution is extracted with 2.5 L of ethyl acetate, the organic phase is discarded, the water phase is cooled to below 10°C, concentrated hydrochloric acid is added dropwise until the pH is 3, and then stirred at 10°C for 30 minutes, a lar...

Embodiment 3

[0063] Embodiment 3, the synthesis of (2,5-dioxazolidin-4-yl) methyl methyl carbonate:

[0064] The reaction process is as follows:

[0065]

[0066] STEP1: Synthesis of N,O-bis(methoxycarbonyl)-L-serine

[0067] Take 1.05Kg (10mol) of L-serine, 10L of 2mol / L sodium hydroxide solution, and 2.12Kg (20mol) of sodium carbonate into a 20L reaction kettle, start stirring, and after the L-serine is completely dissolved, lower the temperature of the solution to - Below 10°C, add dropwise 5L of tetrahydrofuran solution containing 2.84Kg (30mol) of methyl chloroformate, keep the temperature of the solution below 20°C during the dropping process, and react at 60°C for 8h after the drop is complete. After the reaction was completed, the reaction solution was extracted with 3 L of ethyl acetate, the organic phase was discarded, the water phase was cooled to below 10°C, concentrated hydrochloric acid was added dropwise until the pH was 2, and then stirred at 10°C for 30 minutes, a larg...

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Abstract

The invention provides a preparation process of amino acid N-carboxylic acid anhydride, which comprises the following operations: amino acid and methyl chloroformate are used as starting raw materials to react under an alkaline condition to generate N-methoxycarbonyl-amino acid, and the N-methoxycarbonyl-amino acid is separated and purified under an acidic condition; dissolving the purified and dried N-methoxycarbonyl-amino acid in a solvent, mixing with a ring closing reagent thionyl chloride, and reacting at a certain reaction temperature to generate an amino acid N-carboxylic acid anhydride crude product; and adding a good solvent into the obtained amino acid N-carboxylic acid anhydride crude product, filtering to remove impurities, adding a poor solvent into the filtrate, recrystallizing under freezing, and drying to obtain the amino acid N-carboxylic acid anhydride (NCA). The preparation process is simple and convenient in method, easy to purify, stable in process, controllable in quality, low in anhydrous requirement on a reaction system, greatly improved in product yield, greatly reduced in reaction risk and suitable for industrial mass production.

Description

technical field [0001] The invention relates to a preparation process of amino acid N-carboxylic acid anhydride (NCA), belonging to the technical field of chemical synthesis and production. Background technique [0002] Polyamino acid is a kind of biodegradable polymer, which has the advantages of low toxicity, good biocompatibility, biodegradability, easy absorption and metabolism by the body, etc. It is widely used, for example, it can be used to manufacture synthetic fibers, Leather, food packaging film. And through the modification and repolymerization of various amino acids, materials with better performance than ordinary natural fibers and chemical fibers can also be obtained. In addition, polyamino acids and their derivatives can also be used as stabilizers and plasticizers. In particular, it is widely used in the medical field as a biological material, such as medical sutures, packaging materials for medicines, etc. [0003] Although there are many ways to synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/44C07D413/06
CPCC07D263/44C07D413/06
Inventor 罗磊王乐吴军王勇彭佩
Owner JINGCHU UNIV OF TECH
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