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L-glutamic acid derivative and synthesis method and application thereof

A synthesis method and technology of glutamic acid are applied in the field of synthesis of intermediates of medicine and traditional Chinese medicine, and can solve the problems of complicated production process, inability to apply in the field of peptide synthesis, and high energy consumption.

Pending Publication Date: 2020-10-23
四川嘉瑛莱科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many polypeptide drugs and cosmetics contain glutamic acid in the amino acid composition of polypeptides. However, since glutamic acid has two carboxyl groups, namely the 5-position carboxyl group and the 1-position carboxyl group, it is necessary to protect the carboxyl groups at these two positions to form Glutamic acid in the protected form can be used in the synthesis of peptides, while glutamic acid with unprotected carboxyl groups cannot be used in the field of peptide synthesis
[0003] At present, the product produced by the synthesis method in the prior art is an oil, and the high-efficiency liquid phase purity of the product is lower than 90%, while the crystallization yield of the product obtained by the existing process is only about 70%, and the production process is complicated. More equipment, high energy consumption, low yield

Method used

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  • L-glutamic acid derivative and synthesis method and application thereof
  • L-glutamic acid derivative and synthesis method and application thereof
  • L-glutamic acid derivative and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A kind of synthetic method of L-glutamic acid derivative, synthetic method comprises the steps:

[0046](1) Select 300g (2.04mol) of L-glutamic acid (L-Glu-OH) and 1kg (1.25L, 31mol) of methanol (MeOH) into the reaction device for mixing, and add chlorine at 8-10 degrees Celsius Sulfoxide (SOCl 2 ) 250g (2.1mol), then heat the temperature to 30-35 degrees Celsius and keep the constant temperature reaction for 3 hours to obtain the standby solution I;

[0047] (2) Concentrate the stock solution I after the complete reaction to dryness at 40-45 degrees Celsius, and cool to room temperature to obtain L-glutamic acid dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl );

[0048] (3) Add ethyl acetate 1kg (1.1L, 11.36mol) to the L-glutamate dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl) obtained in step (2), Water 200ml, adjust the pH to 9-10 with sodium hydroxide, then add (Boc) 2 O (di-tert-butyl dicarbonate) 440g (2.02mol) was reacted for 3 hours to obtain standby soluti...

Embodiment 2

[0057] A kind of synthetic method of L-glutamic acid derivative, synthetic method comprises the steps:

[0058] (1) Select 300g (2.04mol) of L-glutamic acid (L-Glu-OH) and 1kg (1.25L, 31mol) of methanol (MeOH) into the reaction device for mixing, and add chlorine at 8-10 degrees Celsius Sulfoxide (SOCl 2 ) 250g (2.1mol), then heat the temperature to 30-35 degrees Celsius and keep the constant temperature reaction for 3 hours to obtain the standby solution I;

[0059] (2) Concentrate the stock solution I after the complete reaction to dryness at 40-45 degrees Celsius, and cool to room temperature to obtain L-glutamic acid dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl );

[0060] (3) Add ethyl acetate 1kg (1.1L, 11.36mol) to the L-glutamate dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl) obtained in step (2), 200ml of water, adjust the pH to 9-10 with sodium hydroxide, then add 440g (2.02mol) of di-tert-butyl dicarbonate and react for 3 hours to obtain the standby solution I...

Embodiment 3

[0067] A kind of synthetic method of L-glutamic acid derivative, synthetic method comprises the steps:

[0068] (1) Select 500g (3.4mol) of L-glutamic acid (L-Glu-OH) and 1.7kg (2.2L, 53mol) of methanol (MeOH) and put them into the reaction device for mixing, and add them at 10-12 degrees Celsius Thionyl chloride (SOCl 2 ) 425g (3.6mol), then heated the temperature to 38-40 degrees Celsius and kept the constant temperature reaction for 12 hours to obtain the standby solution I;

[0069] (2) Concentrate the stock solution I after the complete reaction to dryness at 70-80 degrees Celsius and cool to room temperature to obtain L-glutamic acid dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl );

[0070] (3) Add ethyl acetate 1.7Kg (1.9L, 19mol) to the L-glutamate dimethyl hydrochloride oil (L-Glu(ome)-ome.HCl) obtained in step (2), 350ml of water, adjust the pH to 9-10 with sodium hydroxide, then add 740g (3.4mol) of di-tert-butyl dicarbonate and react for 12 hours to obtain the ...

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Abstract

The invention belongs to the technical field of synthesis of medical and traditional Chinese medicine intermediates, and discloses an L-glutamic acid derivative and a synthesis method and applicationthereof. All the steps in the synthesis method are simple and in order , the obtained L-dimethyl glutamate hydrochloride oily matter is directly put into the next step of reaction through a one-pot method, L-dimethyl glutamate hydrochloride solids do not need to be obtained, the use of all the raw materials can be effectively reduced, and the cost is reduced; ethyl acetate is selected as a reaction solvent and can be effectively recycled, the utilization rate of the ethyl acetate is remarkably increased, and pollution to the environment is reduced; a final product is obtained in a crystallization manner so that the convenience and the storage convenience during transportation are improved, and the quality and the yield of the product can be further improved. The technical scheme of the synthesis method is complete and simple, the produced product is high in crystallization yield and better in quality, the overall yield of the product is conveniently, rapidly, scientifically and effectively increased to 85% or above, and raw materials are provided for research and development of new drugs.

Description

technical field [0001] The invention belongs to the technical field of synthesis of traditional Chinese medicine intermediates, and specifically relates to an L-glutamic acid derivative and its synthesis method and application. Background technique [0002] Glutamic acid is an acidic amino acid with two carboxyl groups in its molecule. It exists in a large amount in cereal proteins and plays an important role in the protein metabolism process in organisms. Glutamic acid is one of the amino acids that constitute proteins and is also an important nutrient for humans and animals. Many polypeptide drugs and cosmetics contain glutamic acid in the amino acid composition of polypeptides. However, since glutamic acid has two carboxyl groups, namely the 5-position carboxyl group and the 1-position carboxyl group, it is necessary to protect the carboxyl groups at these two positions to form Glutamic acid in the protected form can be used in the synthesis of peptides, while glutamic a...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/22C07C269/08
CPCC07C227/18C07C269/04C07C269/08
Inventor 杨朝雪唐寅肖斌周虎向暑张敬科
Owner 四川嘉瑛莱科技有限责任公司
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