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L-alanyl-L-glutamine compound and synthetic method thereof

A technology of glutamine and a synthesis method, applied in the field of medicine, can solve the problems of complex synthesis process, high production cost, low yield harm and the like, and achieve the effects of simple synthesis process, improved yield, and few reaction by-products

Inactive Publication Date: 2009-09-02
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the present invention is to provide a simple process, low cost and high yield in order to overcome the disadvantages of complex synthesis process, great harm to human body and high production cost of L-alanyl-L-glutamine compound in the prior art. Synthetic method of high and less harmful L-alanyl-L-glutamine compound

Method used

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  • L-alanyl-L-glutamine compound and synthetic method thereof
  • L-alanyl-L-glutamine compound and synthetic method thereof

Examples

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Embodiment 1

[0025] (1) Under the environment of nitrogen protection at -18°C, 65 grams of isobutyl chloroformate (0.48 moles) were added to 300 milliliters of a solution of 59 grams of N-formyl L-alanine (0.5 moles) in tetrahydrofuran , then 48 gram of N-methylmorpholine (0.48 moles) are added dropwise to the solution, the rate of addition is controlled so that the temperature of the solution is no more than -15°C, a precipitate is formed, and after continuous stirring for 20 minutes, 66 gram of L-glutamine ( 0.45 mol) of tetrahydrofuran solution (300 ml), keep the reaction temperature not exceeding -15°C when adding, and then stir at -18°C for 1 hour. The reaction mixture was warmed up to 0° C., 500 grams of water was added at this temperature, and then tetrahydrofuran was distilled off under vacuum, 300 milliliters of isopropyl acetate was added, and the pH value of the reaction mixture was adjusted to 1.5 with 5 mol / liter hydrochloric acid. After the layers were separated, they were ex...

Embodiment 2

[0030](1) Under the environment of nitrogen protection at -18°C, 86.67 grams of isobutyl chloroformate (0.64 moles) were added to 400 milliliters of a tetrahydrofuran solution of 78.67 grams of N-formyl L-alanine (0.67 moles). , then 64 gram of N-methylmorpholine (0.64 moles) are added dropwise to the solution, the rate of addition is controlled so that the temperature of the solution is no more than -15°C, a precipitate is formed, and after continuous stirring for 20 minutes, 88 gram of L-glutamine ( 0.6 mol) of tetrahydrofuran solution (400 ml), keep the reaction temperature not exceeding -15°C when adding, and then stir at -18°C for 1 hour. The reaction mixture was warmed up to 0° C., 600 grams of water was added at this temperature, tetrahydrofuran was then distilled off under vacuum, 400 milliliters of isopropyl acetate was added, and the pH value of the reaction mixture was adjusted to 1.5 with 1 mol / liter of hydrochloric acid. After the layers were separated, they were ...

Embodiment 3

[0035] (1) Under the environment of nitrogen protection at -18°C, 130 grams of isobutyl chloroformate (0.96 mole) was added to 600 milliliters of a solution of 118 grams of N-formyl L-alanine (1 mole) in tetrahydrofuran , then 96 gram of N-methylmorpholine (0.96 moles) are added dropwise to the solution, the rate of addition is controlled so that the temperature of the solution is no more than -15°C, a precipitate is formed, and after continuous stirring for 20 minutes, 132 gram of L-glutamine ( 0.9 mol) of tetrahydrofuran solution 600ml, keep the reaction temperature not exceeding -15°C when adding, and then stir at -18°C for 1 hour. The reaction mixture was warmed up to 0° C., 1000 grams of water was added at this temperature, tetrahydrofuran was then distilled off under vacuum, 600 milliliters of isopropyl acetate was added, and the pH value of the reaction mixture was adjusted to 1.5 with 3 mol / liter hydrochloric acid. After the layers were separated, they were extracted t...

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Abstract

The invention aims to overcome the defects of complicated synthetic process, great harm to human body and high production cost of L-alanyl-glutamine compound in the prior art, and the synthetic method of the L-alanyl-glutamine compound with simple process, low cost, high productivity and less harm is provided. The invention provides the synthetic method of the L-alanyl-L-glutamine compound, which comprises the following steps: (1) adding a chloroformate isobutyl ester to a tetrahydrofuran solution of N-formacyl L-alanine to obtain N-formacyl-L-alanyl-L-glutamine, and (2) suspending the N-formacyl-L-alanyl-L-glutamine in hydrochloric acid to prepare the L- alanyl-L-glutamine compound.

Description

technical field [0001] The invention relates to a synthesis method of L-alanyl-L-glutamine compound, which belongs to the technical field of medicine. Background technique [0002] L-alanyl-L-glutamine, molecular formula: C 8 h 15 N 3 o 4 , molecular weight: 217.22, structural formula: [0003] [0004] L-alanyl-L-glutamine (CAS: 393570-23-0) belongs to amino acid derivatives, and is currently a popular amino acid dipeptide product at home and abroad. Ideal substitute for glutamine, the most abundant amino acid. L-alanyl-L-glutamine has high solubility, 200 times that of free glutamine under the same conditions, and is stable in nature, and will not produce toxic pyroglutamine under different pH conditions for heat sterilization Acid and ammonia are produced. After L-alanyl-L-glutamine enters the body, it is rapidly and effectively decomposed into alanine and glutamine by dipeptidases in many organs and tissues to meet the needs of the body without any toxic side e...

Claims

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Application Information

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IPC IPC(8): C07K5/062
Inventor 张锡芬
Owner HAINAN LINGKANG PHARMA CO LTD
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