Method for preparing amino acid N-carboxyanhydride

A technique for intracyclic acid anhydride and amino acid, applied in the field of preparing amino acid N-carboxy intracyclic acid anhydride, can solve the problems of reduced yield, low yield and the like, and achieve the effects of improving yield, improving decomposition rate and shortening reaction time

Inactive Publication Date: 2013-07-17
HYBIO PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Although the most commonly used method in the industry is to use triphosgene instead of phosgene and amino acids to prepare amino acid-NCA, because triphosgene needs to be decomposed into phosgene before the condensation reaction in th...

Method used

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  • Method for preparing amino acid N-carboxyanhydride

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Embodiment

[0025] The present invention will be illustrated in more detail by the following examples, but these examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

Embodiment 1

[0029]Put 25 grams of L-alanine, 0.5 grams of activated carbon and 450 milliliters of anhydrous tetrahydrofuran into the above-mentioned reaction device. At 50 ° C, add dropwise 50 milliliters of anhydrous tetrahydrofuran solution containing 33.4 grams of triphosgene. After the addition is complete, After stirring at this temperature for 3 hours, the system was almost clear. The reaction mixture was filtered with celite filter aid. The filtrate was concentrated to one-fifth of the original volume, 2 liters of petroleum ether was added, and the crude product was obtained by filtration. Recrystallization from a mixed solvent of ethyl acetate and petroleum ether gave 21 g of a white solid, melting point: 91-92°C.

Embodiment 2

[0031] Put 25 grams of L-alanine, 0.25 grams of activated carbon and 450 milliliters of anhydrous tetrahydrofuran into the above-mentioned reaction device. At 50° C., add dropwise 50 milliliters of anhydrous tetrahydrofuran solution containing 27.8 grams of triphosgene. After the addition is complete, After stirring at this temperature for 5 hours, the system was almost clear. The reaction mixture was filtered with celite filter aid. The filtrate was concentrated to one-third of the original volume, 250 ml of petroleum ether was added, and the crude product was obtained by filtration. Recrystallization from a mixed solvent of ethyl acetate and petroleum ether gave 7 g of a white solid, melting point: 91-92°C.

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Abstract

The invention provides a method for preparing amino acid N-carboxyanhydride. The method includes enabling amino acid to react with triphosgene to generate the corresponding amino acid N-carboxyanhydride in the presence of triphosgene decomposition catalysts under the condition that anhydrous tetrahydrofuran is used as a solvent. The method has the advantages that the triphosgene decomposition catalysts are utilized and are beneficial to increasing the decomposition rate of the triphosgene, accordingly, the reaction time is shortened, the yield of the amino acid-NCA (N-carboxyanhydride) is increased, and the reaction yield is particularly greatly increased when R-groups of the amino acid are short.

Description

technical field [0001] The invention relates to a method for preparing an acid anhydride in an amino acid N-carboxyl ring. Background technique [0002] Chemically synthesized polyamino acids or peptides are a class of biopolymer materials with structures similar to natural proteins or peptides. The polyamino acid obtained by homopolymerization or copolymerization of amino acid not only has excellent mechanical properties, but also has low toxicity, good biocompatibility and biodegradability. Therefore, polyamino acid exhibits better performance than ordinary natural fibers and chemical fibers, and is widely used in various fields such as industry, agriculture, and medicine, especially in the field of biomedical materials, showing unique medicinal value. Among the many methods for synthesizing polyamino acids at present, the ring-opening polymerization using amino acid N-Carboxy Anhydride (NCA for short) has become the most important way to prepare polyamino acids. After W...

Claims

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Application Information

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IPC IPC(8): C07D263/44
Inventor 李国弢韦畅勇马亚平袁建成
Owner HYBIO PHARMA
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