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Synthetic method of L-carnosine

A synthesis method and carnosine technology, applied in the field of L-carnosine synthesis, can solve the problems of difficulty in meeting high-quality requirements of products, difficulty in industrialized production, and high solvent consumption, reducing the generation of by-products, shortening reaction steps, and shortening reaction steps. Effect

Active Publication Date: 2017-04-19
HUBEI HUNTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The yield of the L-carnosine product obtained by the above synthetic method is below 85%. Because hydrazine hydrate is used to remove the phthaloyl protecting group, there are residues of hydrazine in the product, so it is difficult to reach the high-quality requirement of hydrazine-free in the product. And the solvent consumption is too high, and the by-products are more, causing environmental pollution, so industrial production is more difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of 3-chloropropionyl chloride (II).

[0036] In a 1000ml reaction bottle, add 52.6g 3-chloropropionic acid (0.485mol), 500ml toluene, 72.0g triphosgene (0.485mol), slowly raise the temperature to 25°C, keep it warm for 8h, the material is a transparent liquid, and then recover toluene under reduced pressure, Evaporate to dryness to obtain 60.7 g of product (II), the yield is 98.5%. Add 500 ml of chloroform, stir and dissolve at room temperature, and obtain a light yellow transparent liquid, which is used for the following condensation reaction.

Embodiment 2

[0038] Preparation of 3-chloropropionyl chloride (II).

[0039] In a 500ml reaction bottle, add 26.3g 3-chloropropionic acid (0.242mol), 250ml toluene, 57.7g thionyl chloride (0.484mol), slowly raise the temperature to 20°C, keep it warm for 10h, the material is a transparent liquid, and then recover under reduced pressure Toluene was evaporated to dryness to obtain 30.1 g of product (II), with a yield of 98.0%. Add 250 ml of chloroform and stir to dissolve at room temperature to obtain a light yellow transparent liquid, which is used for the following condensation reaction.

Embodiment 3

[0041] Preparation of the amide product of L-histidine protected compound and 3-chloropropionyl chloride (Ⅲ)

[0042] In a 1000ml reaction flask, add 50g of trimethylsilane-protected L-histidine (0.323mol), add 600ml of chloroform and stir. At this time, the material is a transparent liquid. Cool down to 5°C, and then slowly add dropwise the The chloroform solution of 3-chloropropionyl chloride (0.484mol), the reaction temperature is 10-20°C, and the reaction is stirred overnight for 20h to obtain the product (Ⅲ).

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Abstract

The invention discloses a synthetic method of L-carnosine, and belongs to the technical field of organic matter synthesis. The method comprises the following steps: dissolving 3-chloropropionic acid in an organic solvent, and converting the 3-chloropropionic acid by a chloroformylation reagent to form corresponding 3-chloropropionyl chloride; condensing trimethylsilane protected L-histidine and the 3-chloropropionyl chloride to obtain a corresponding amide product; removing protection agents by using water or an alkaline solution to obtain an intermediate; carrying out aminolysis on the intermediate to obtain crude L-carnosine; and purifying the crude L-carnosine to obtain finished L-carnosine. The synthetic method has the advantages of low raw material consumption, short reaction steps, few wastes, high yield, obtaining of high-quality L-carnosine free from hydrazine, and meeting of industrial production demands.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of L-carnosine. Background technique [0002] L-carnosine (L-carnosine) is a natural dipeptide, and the chemical name of L-carnosine is β-alanyl-L-histidine. Its structural formula is as follows: [0003] [0004] L-carnosine was discovered as early as 1900, and it mainly exists in the skeletal muscles and brains of vertebrates, such as pork, beef, muscle, etc., especially the content in chicken breast is particularly high. In humans, the substance exists in higher concentrations in the most active parts of aerobic metabolism, such as muscles and brain. Its chemical nature is produced by the action of β-alanyl and L-histidine through carnosine synthase. Research reports show that carnosine not only has excellent natural anti-oxidation, anti-free radical and anti-aging effects, but also has the beneficial effect of reversing ...

Claims

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Application Information

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IPC IPC(8): C07D233/64
CPCY02P20/55C07D233/64
Inventor 许天亮娄明汪黎民雷玉平张锐李健雄
Owner HUBEI HUNTIDE BIOTECH
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