A kind of preparation method of alanyl glutamine

A technology of alanyl glutamine and alanyl succinimide, which is applied in the field of preparation of alanyl glutamine, can solve problems such as difficult removal, short process steps, human harm and the like, and achieves increased yield, Easy to handle and the effect of promoting precipitation

Active Publication Date: 2020-11-27
CISEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process steps are short, but vigorous stirring is required, and the reaction is easy to produce by-products such as tripeptides and tetrapeptides that are difficult to remove; phosgene is a toxic gas, and it is harmful to the human body when the reaction is incomplete.

Method used

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  • A kind of preparation method of alanyl glutamine
  • A kind of preparation method of alanyl glutamine
  • A kind of preparation method of alanyl glutamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of chloro-Boc-alanine:

[0021]

[0022] Add Boc-alanine (18.9g, 0.1mol) into the reaction flask, then add thionyl chloride (17.9g, 0.15mol), then add N,N-dimethylformamide (0.7g, 0.01mol ) stirred at 75°C-85°C for 5h, then cooled to 40-50°C, controlled the temperature at 45-55°C and concentrated under reduced pressure until no distillate was obtained, and the obtained oil was directly used in the next reaction.

[0023] Preparation of Boc-alanylsuccinimide:

[0024]

[0025] N-hydroxysuccinimide (13.8g, 0.12mol) was dissolved in 90ml of acetone, then triethylamine (50.5g, 0.5mol) was added, and chloro-Boc-alanine (0.1mol ) was dissolved in 40ml of acetone and added dropwise to the above system. After the addition was completed, it was reacted at room temperature for 4 hours, and then 400g of purified water was added to the reaction system, a large amount of solids would be precipitated, filtered with suction, and the filter cake was rinsed with purif...

Embodiment 2

[0033] Preparation of chloro-Boc-alanine:

[0034]

[0035] Add Boc-alanine (18.9g, 0.1mol) into the reaction flask, then add thionyl chloride (17.9g, 0.15mol), then add N,N-dimethylformamide (0.7g, 0.01mol ) stirred at 75°C-85°C for 5h, then cooled to 40-50°C, controlled the temperature at 45-55°C and concentrated under reduced pressure until no distillate was obtained, and the obtained oil was directly used in the next reaction.

[0036] Preparation of Boc-alanylsuccinimide:

[0037]

[0038] N-hydroxysuccinimide (13.8g, 0.12mol) was dissolved in 90ml of acetone, then triethylamine (50.5g, 0.5mol) was added, and chloro-Boc-alanine (0.1mol ) was dissolved in 40ml of acetone and added dropwise to the above system. After the addition was completed, it was reacted at room temperature for 4 hours, and then 400g of purified water was added to the reaction system, a large amount of solids would be precipitated, filtered with suction, and the filter cake was rinsed with purif...

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Abstract

The present invention relates to a method for preparing alanyl-glutamine. The method comprises the following steps: reaction of Boc-Alanine in the presence of thionyl chloride to obtain acyl chloride; reaction of the acyl chloride and N-hydroxysuccinimide under alkaline conditions to obtain Boc-Alanyl succinimide, and further reaction of the Boc-Alanyl succinimide with glutamine to obtain Boc-Alanyl glutamine; and hydrolysis of the Boc-Alanyl glutamine to obtain the alanyl-glutamine. Compared with the prior art, the method has the following effects: the Boc-Alanine is reacted in the presence of the thionyl chloride to obtain the acyl chloride, the raw material is cheap and wide, and operation is simple; the acyl chloride and the N-hydroxysuccinimide are reacted under the alkaline conditions to obtain an active intermediate, the reaction postprocessing is simple, the active intermediate does not need to be refined; the synthetic route is short, the high purity alanyl-glutamine can be prepared, and a powerful guarantee is provided for the industrial production of the alanyl-glutamine and intermediates thereof.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and in particular relates to a preparation method of alanyl glutamine. Background technique [0002] The molecular formula of alanylglutamine is C8H15N3O4, which is a white or off-white loose lump. As a parenteral nutrition drug, it can be used to improve the patient's cellular immune function and effectively reduce the risk of infection in critically ill patients, especially for severe infections and malignant tumors. The treatment and recovery of critically injured patients plays an important role in reducing the total length of hospital stay for patients. CG dipeptide is widely used in foreign countries. Since its introduction in my country, its market demand is increasing and the market prospect is broad. Alanyl glutamine, its structure is as follows: [0003] [0004] The synthesis method reported in the literature has the DCC coupling method, Boc-alanine and N-hydroxysucci...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/062C07K1/06
CPCC07K5/06026
Inventor 张乐波孙品卢秀莲
Owner CISEN PHARMA
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