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Artificial synthesis method of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid

A pyrimidine carboxylic acid, artificial synthesis technology, applied in 1 field, to achieve the effect of simple synthesis process steps and little environmental pollution

Inactive Publication Date: 2010-04-28
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the above-mentioned prior art, the present invention provides a method for the artificial synthesis of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, the process is simple and the yield is high, and it can be produced on a large scale , to meet the needs of society

Method used

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  • Artificial synthesis method of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
  • Artificial synthesis method of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid

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Embodiment 1

[0027] Example 1 Synthetic preparation of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, the steps are as follows:

[0028] (1) Mix 4-nitrophenol acetate (3.62g, 20mmol) with NaOH (1.68g, 40mmol), add to 200ml L-2,4-diaminobutyric acid aqueous solution (0.1mmol / ml), at 25°C Stirring at 80rpm for 14 hours, after the completion of the reaction, with CH 2 Cl 2 Extraction was carried out, the extract was dried with anhydrous sodium sulfate, and CH was distilled off under reduced pressure. 2 Cl 2 and the remaining 4-nitrophenol acetate, and vacuum-dried at 50°C for 4 hours to obtain a mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid.

[0029] (2) Dissolve the mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid in 80ml of n-butanol, add 2g of triethylamine, heat and reflux at 80°C for 48 hours, and depressurize The organic solvent was evaporated, and column chromatography (200-300 mesh silica gel) was performed w...

Embodiment 2

[0035] Example 2 Artificially synthesized 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, the steps are as follows:

[0036] (1) Mix 4-nitrophenol acetate (5.43g, 30mmol) with KOH (2.25g, 40mmol), add to 200ml L-2,4-diaminobutyric acid aqueous solution (0.1mmol / ml), at 25°C Stirring at 80rpm for 12 hours, after the completion of the reaction, with CH 2 Cl 2 Extraction was carried out, the extract was dried with anhydrous sodium sulfate, and CH was distilled off under reduced pressure. 2 Cl 2 and the remaining 4-nitrophenol acetate, and vacuum-dried at 50°C for 4 hours to obtain a mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid.

[0037] (2) Dissolve the mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid in 100ml of ethanol, add 2g of triethylamine, heat and reflux at 120°C for 48 hours, evaporate under reduced pressure Organic solvent, column chromatography (200-300 mesh silica gel) with n-butanol / acetic a...

Embodiment 3

[0043] Example 3 Artificially synthesized 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, the steps are as follows:

[0044] (1) Mix 4-nitrophenol acetate (5.43g, 30mmol) with NaOH (1.68g, 40mmol), add to 200ml L-2,4-diaminobutyric acid aqueous solution (0.1mmol / ml), at 30°C Stirring at 80rpm for 14 hours, after completion of the reaction, with CH 2 Cl 2 Extraction was carried out, the extract was dried with anhydrous sodium sulfate, and CH was distilled off under reduced pressure. 2 Cl 2 and the remaining 4-nitrophenol acetate, and vacuum-dried at 50°C for 4 hours to obtain a mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid.

[0045] (2) Dissolve the mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamidobutyric acid in 80ml of n-butanol, add 2g of triethylamine, heat and reflux at 120°C for 36 hours, and depressurize The organic solvent was evaporated, and column chromatography (200-300 mesh silica gel) was performed with...

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Abstract

The invention discloses an artificial synthesis method of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, comprising the following steps: (1) taking 4-nitrophenol acetate and inorganic base, then mixing, adding the mixture into L-2,4-diaminobutyric acid water solution for reaction along with stirring to generate the mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamido aminobutyric acid, and then extracting with CH2Cl2 to obtain the extractive liquid, drying, reducing pressure for distilling, carrying out vacuum drying to obtain the mixture of 2-acetamido-4-aminobutyric acid and 2-amino-4-acetamido aminobutyric acid; and (2) dissolving the above reaction mixture in polar organic solvent, then adding triethylamine, heating and refluxing, reducing pressure to evaporate the organic solvent, then using column chromatography to purify the mixture to obtain the 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid. The synthesis process of the invention has simple steps, little environment pollution, and 50%-70% of yield, thus being applicable to industrial production.

Description

technical field [0001] The present invention relates to a synthesis method of cyclic amino acid with physiological activity, in particular to the artificial synthesis method of 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid. Background technique [0002] 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid (L-ectoine, CAS No.: 96702-03-3) is a photosynthetic species of the extreme halophilic Exochorhodospira in 1985. A novel cyclic amino acid discovered in the purple bacterium Halochloris is a compatible solute produced intracellularly by salt-tolerant microorganisms to maintain osmotic pressure balance. With the application of nuclear magnetic resonance and high performance liquid phase analysis techniques, more and more experiments have proved that 1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid is not only a moderate halophilic bacteria and The main compatible solute for halophilic bacteria can also be detected in non-halophilic bacteria such as acti...

Claims

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Application Information

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IPC IPC(8): C07D239/06
Inventor 厉保秋
Owner SHANDONG UNIV
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