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Preparation method for chiral L-alanyl-phenylalanine

A technology of chiral phenylalanine and phenylalanine, applied in the direction of peptides, etc., can solve the problem of unreported L-alanyl-phenylalanine, etc., and achieve easy post-processing, readily available raw materials, and low cost Effect

Inactive Publication Date: 2017-04-19
HUBEI HUNTIDE BIOTECH
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  • Abstract
  • Description
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Problems solved by technology

[0005] At present, the synthesis method and route of L-alanyl-phenylalanine have not been reported in China. This patent reports that D-2-chloropropionyl chloride is condensed into an amide with the amino group of phenylalanine in a solvent, and then aminolysis The product is obtained under mild conditions and high yield, which is very suitable for industrial production

Method used

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  • Preparation method for chiral L-alanyl-phenylalanine

Examples

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Embodiment 1

[0032] Preparation of 2-chloropropionyl-L-phenylalanine

[0033] In a 500mL reaction flask, add 165mL of chloroform, 16.5g of L-phenylalanine (0.1mol), 30.3g of triethylamine (0.3mol), and dropwise add 25.4g of D-2-chloropropionyl chloride (0.2mol) at room temperature, The pH value of the reaction is stable between 8-10, and the raw materials are completely reacted after 5 hours of reaction. Then lower the temperature to 1-5°C, adjust the pH to 1-2 with hydrochloric acid, stir for 1 hour, filter with suction, and dry the solid to obtain 23.7 g of product (I), the yield is 93.2%, and the HPLC purity is ≥97%.

Embodiment 2

[0035] Preparation of 2-chloropropionyl-L-phenylalanine

[0036] In a 250mL reaction flask, add 90mL of butyl acetate, 8.25g of L-phenylalanine (0.05mol), 27.6g of potassium carbonate (0.2mol), drop 19g of D-2-chloropropionyl chloride (0.15mol) at room temperature, and react The pH value is between 9-11, and the raw materials are completely reacted after 7 hours of reaction. Cool down to 10-15°C, adjust the pH to 2-3, stir for 1 hour, filter with suction to obtain a solid, and dry to obtain 12.1 g of the product. The yield is 94.5%, and the HPLC purity is 97.7%.

Embodiment 3

[0038] Preparation of 2-chloropropionyl-D-phenylalanine

[0039] In a 2000mL reaction flask, add 543g of water and 132g of sodium hydroxide (3.3mol), stir to dissolve, cool down to room temperature, then add 165g of D-phenylalanine (1mol), dropwise add 381g of D-2- Chloropropionyl chloride (3mol), the reaction pH value is between 9-12, react for 8 hours, the raw materials are completely reacted, separate the liquid to take the water layer, cool down to 1-5°C, adjust the pH to 1-2, stir for 1 hour, and filter to obtain a solid , and dried to obtain 241.6 g of the product 2-chloropropionyl-D-phenylalanine, the yield was 94.5%, and the HPLC purity was 98.2%.

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Abstract

The invention discloses a preparation method for chiral L-alanyl-phenylalanine, belonging to the technical field of synthesis of organic matters. The method comprises the following steps: subjecting L-phenylalanine, D-phenylalanine or DL-phenylalanine and D-2-chloropropionyl chloride to condensation so as to obtain 2-chloropropionyl-phenylalanine with a corresponding configuration; carrying out ammoniation on 2-chloropropionyl-phenylalanine so as to obtain a crude L-alanyl-phenylalanine product with a corresponding configuration; and purifying the crude product so as to obtain finished L-alanyl-L-phenylalanine, L-alanyl-D-phenylalanine or L-alanyl-DL-phenylalanine. The method provided by the invention is low in raw material consumption and high in yield; and prepared chiral L-alanyl-phenylalanine has high quality and can meet requirements of industrial production.

Description

technical field [0001] The invention belongs to the technical fields of medicines, medicine intermediates and chemical engineering, and in particular relates to a preparation method of chiral L-alanyl-phenylalanine. Background technique [0002] The English name of L-alanyl-phenylalanine is H-ALA-PHE-OH, and its chemical name is L-alanyl-phenylalanine. It is a white crystalline solid with the following structure: [0003] [0004] L-alanyl-phenylalanine is metabolized into phenylalanine in the body, and L-phenylalanine is a nutritional supplement and one of the essential amino acids. It can be added to baked food. In addition to strengthening phenylalanine, it can react with sugars in the amino-carbonyl group to improve food aroma. Its physiological role is related to tyrosine. May affect thyroid hormones and melanin in hair and skin. The D-type has the same physiological effect as the L-type. The minimum requirement (mg / kg / d): 31 for adult men; 169 for young children...

Claims

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Application Information

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IPC IPC(8): C07K5/062C07K1/36C07K1/34C07K1/30C07K1/02
CPCC07K5/06026
Inventor 黄发勋周泉汪黎明李健雄
Owner HUBEI HUNTIDE BIOTECH
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