Synthesis method of N-(2-chloride)-propionyl-glutamine

A technology of glutamine and synthetic method, which is applied in the field of synthesis of N-(2-chloro)-propionyl-glutamine, can solve the problems of low yield and long route, and achieve high product yield and simple process Feasible, simple and novel synthesis route

Inactive Publication Date: 2013-12-25
CHONGQING TECH & BUSINESS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The invention is used to solve the problems of long route and low yield in the existing synthetic method of N-(2-chloro)-propionyl-glutamine

Method used

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  • Synthesis method of N-(2-chloride)-propionyl-glutamine

Examples

Experimental program
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Embodiment 1

[0018] Step a, synthetic D-(+)-2-chloropropionic acid ethyl ester

[0019] Take 250 g (2.12 moles) of L-ethyl lactate in a dry three-necked bottle, o Add 2 grams of catalyst 2-methylquinoline (or 4-methylquinoline, quinoline, isoquinoline, indole, indazole, imidazole, benzimidazole, pyrrole, piperazine) below C, and then drop 262 g (2.2 moles) of thionyl chloride, keeping the temperature at 10 o Below C, after the dropwise addition, at 5 o Stir for 1 hour below C, then raise the temperature to 50 o C , stirred for 3 hours, cooled the reaction solution to 30 o C. HCl, SO2, and SOCl2 were removed under reduced pressure, and rectification was carried out after the gas was exhausted to obtain D-(+)-2-chloropropionic acid ethyl ester product with a yield of 96%. The product purity reaches 99.8%, and the optical purity reaches 99.5%.

[0020] Step b, synthesis of D-(+)-2-chloropropionic acid

[0021] Take 100 grams (0.73 moles) of ethyl D-(+)-2-chloropropionate, at 0 o St...

Embodiment 2

[0026] Step a, synthetic D-(+)-2-chloropropionic acid ethyl ester

[0027] Take 530 grams (4.45 moles) of thionyl chloride in a dry three-necked flask, o Add dropwise 500 grams (4.24 moles) of L-ethyl lactate and 4 grams of catalyst 2-methylquinoline (or 4-methylquinoline, quinoline, isoquinoline, indole, indazole, imidazole, benzene and imidazole, pyrrole, piperazine) mixture, keep the temperature at 10 o Below C, after the dropwise addition, at 5 o Stir for 1 hour below C, then raise the temperature to 50 o C , stirred for 5 hours, cooled the reaction solution to 30 o C. HCl, SO2, and SOCl2 were removed under reduced pressure, and rectification was carried out after the gas was exhausted to obtain D-(+)-2-chloropropionic acid ethyl ester product with a yield of 93%. The product purity reaches 99.5%, and the optical purity reaches 98.5%.

[0028] Step b, synthesis of D-(+)-2-chloropropionic acid

[0029] Take 500 grams (3.66 moles) of ethyl D-(+)-2-chloropropionate, at ...

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Abstract

The invention discloses a synthesis method of N-(2-chloride)-propionyl-glutamine. The synthesis method comprises the steps of reacting L-ethyl lactate with thionyl chloride under the presence of catalyst, distilling reaction liquor into alkaline liquor for hydrolyzing to obtain 2-chloropropionic acid; reacting the 2-chloropropionic acid with L-glutamine to obtain N-(2-chloride)-propionyl-glutamine under the presence of the catalyst, and other steps. The synthetic route is simple, the synthesis method is novel, simple and convenient in technique, and high in product yield and purity, the catalyst is low-cost and easily available, the environment is not influenced, and N-(2-chloride)-propionyl-glutamine is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of N-(2-chloro)-propionyl-glutamine. Background technique [0002] N-(2-chloro)-propionyl-glutamine is an important intermediate in the synthesis of N(2)-L-alanyl-L-glutamine (Lipeptide). Because L-glutamine is the amino acid with the most content in human blood, it has important physiological functions, but because of its low solubility and poor thermal stability, L-glutamine is easily decomposed into pyroglutamic acid and ammonia in aqueous solution, which is harmful to the body. Harmful, thus limiting the clinical application of L-glutamine. N(2)-L-alanyl-L-glutamine has high solubility in aqueous solution, can withstand high temperature disinfection, has good stability, and can be rapidly decomposed into L-glutamine and L-propanol in the human body. Amino acid makes up for the deficiency of L-glutamine, so it is widely used as a substitute for L-glutamine in clinical practice. In the prior art, the syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/22C07C231/02
Inventor 蒋和雁
Owner CHONGQING TECH & BUSINESS UNIV
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