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(S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

A tetrahydromethylpyrimidine and synthetic method technology, applied in the field of cyclic amino acid synthesis, can solve the problems of low environmental pollution, retention, and low yield, and achieve the effects of controllable process, stable reaction, and high product yield

Inactive Publication Date: 2017-07-04
上海予利生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the technical scheme announced by the above-mentioned patent, the synthesis process steps of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid are simple, and the environmental pollution is small, but its yield is low, and only stays at In the stage of laboratory research, there is still a long way to go before industrialized production

Method used

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  • (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

Examples

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Effect test

Embodiment 1

[0048] Synthesis of tert-butoxycarbonyl-L-glutamine:

[0049] In the 500ml reaction flask, drop into 10 grams of glutamine, 200 milliliters of 10% sodium carbonate solution, stir and dissolve, add 100 milliliters of acetone, then add dropwise the mixed solution of 30 grams of di-tert-butyl dicarbonate and 20 milliliters of acetone at room temperature, simultaneously Constantly adjust the pH to 8-9 with sodium carbonate, and react overnight at room temperature. Adjust the pH to 2 with 3N hydrochloric acid, then extract 5 times with ethyl acetate, combine the ethyl acetate, wash with saturated brine three times, and evaporate the ethyl acetate to obtain 12 g of tert-butoxycarbonyl-L-glutamine. Melting point: 206-208°C.

Embodiment 2

[0051] Synthesis of Benzyloxycarbonyl-L-Glutamine:

[0052]Put 30 grams of glutamine and 500 milliliters of 10% sodium carbonate solution into a 1L reaction bottle, stir to dissolve, add 300 milliliters of acetone, then add 60 grams of benzyl chloroformate dropwise at room temperature, and continuously adjust the pH to 8- 9. React overnight at room temperature. Use 3N hydrochloric acid to adjust the pH to 2, then extract 5 times with ethyl acetate, combine the ethyl acetate, wash with saturated brine three times, then evaporate the ethyl acetate to obtain 50 g of benzyloxycarbonyl-L-glutamine. Melting point: 135-137°C.

Embodiment 3

[0054] Synthesis of p-toluenesulfonyl-L-glutamine:

[0055] Put 20 grams of glutamine and 200 milliliters of 10% sodium carbonate solution into a 500ml reaction bottle, stir to dissolve, add 100 milliliters of acetone, then add dropwise the mixed solution of 40 grams of p-toluenesulfonyl chloride and 50 milliliters of acetone at room temperature, while constantly using Adjust the pH to 8-9 with sodium carbonate, and react overnight at room temperature. Adjust the pH to 1 with 3N hydrochloric acid, then extract 5 times with ethyl acetate, combine the ethyl acetate, wash with saturated brine three times, and evaporate the ethyl acetate to obtain 32 g of p-toluenesulfonyl-L-glutamine. Melting point: 146-148°C.

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Abstract

The present invention relates to a (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method. According to the method, L-glutamine is used as a raw material, the alpha-amino of the L-glutamine is protected with a protection group, a decarbonylating agent is added, a Hofmann degradation reaction is performed to remove the carbonyl group attached to the remaining amino, the protection group is removed to obtain L-2,4-diaminobutyric acid, and finally the prepared L-2,4-diaminobutyric acid and trimethyl orthoacetate are subjected to a ring forming reaction to obtain the (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Compared to the method in the prior art, the method of the present invention has the following characteristics that the chemical synthesis route is provided, the steps of the synthesis process are simple, the raw materials are easy to obtain, the product purity is high, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of cyclic amino acid synthesis, and relates to a synthesis method of (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid, in particular to a (S) The chemical synthesis method of )-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Background technique [0002] (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid, its chemical structural formula is as follows: [0003] [0004] It is an osmotic pressure compensating solute buffer and emollient, which belongs to natural substances. It was first discovered in microorganisms and can accumulate in its cells through in vivo synthesis and in vitro transport to resist and regulate its own excessive salt. , to maintain the balance of osmotic pressure inside and outside the cell. It can be extracted as an active ingredient of the skin and added to skin care and protection products to stabilize protein and cell structure and reduce dam...

Claims

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Application Information

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IPC IPC(8): C07D239/06
CPCC07B2200/07C07D239/06Y02P20/55
Inventor 金健林
Owner 上海予利生物科技股份有限公司
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