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Preparation method of pyridoxal 5-phosphate monohydrate

A technology of pyridoxal phosphate and pyridoxal hydrochloride, which can be used in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., and can solve the problems of low yield, by-products, aldehyde group oxidation, etc. problems, to achieve high yield, reduce production costs, and solve the effects of crystallization difficulties

Inactive Publication Date: 2019-07-16
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this process, inorganic acid is used to adjust the pH, and inorganic salts (such as sodium chloride, potassium chloride, etc.) will be produced. High salt content of pyridoxal
In addition, the precipitated pyridoxal phosphate crystals are desalted by adding n-propanol for recrystallization, and the yield is low
Moreover, during the recrystallization process, heating will oxidize the aldehyde group, forming a by-product

Method used

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  • Preparation method of pyridoxal 5-phosphate monohydrate
  • Preparation method of pyridoxal 5-phosphate monohydrate

Examples

Experimental program
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Effect test

Embodiment 1

[0023] The preparation method of pyridoxal phosphate, the specific steps are as follows:

[0024] 1. Synthesis of Schiff base of pyridoxal hydrochloride:

[0025]

[0026] 1) Synthesis of pyridoxal hydrochloride: add 5.0g (24.3mmo1) of pyridoxine hydrochloride to 50.0mL of 5.0% dilute hydrochloric acid solution, stir until it is clear, control the temperature at 20.0℃, and add 2.1g ( 24.3mmo1) Manganese dioxide, after 0.5h, add 2.1g (24.3mmol) of manganese dioxide and react for 6.0h to obtain pyridoxal hydrochloride. 2) Synthesis of pyridoxal hydrochloride Schiff base: suction filter the pyridoxal hydrochloride synthesized in step 1) to remove unreacted manganese dioxide, add 12.3g (51.0mmo1) sodium sulfide nonahydrate to the filtrate and stir 0.5h, suction filtration, adjust the pH of the solution to weak acidity, slowly add 6.3g (46.2mmol) p-ethoxyaniline dropwise at 17.0℃, and continue to stir for 1.0h after the completion of the dripping. An orange-yellow solid is formed, suct...

Embodiment 2

[0044] The specific steps for the synthesis of pyridoxal phosphate are as follows:

[0045] 1. Synthesis of pyridoxal hydrochloride Schiff base, the specific steps are the same as step 1 of Example 1;

[0046] 2. For the synthesis of pyridoxal phosphate Schiff base, the specific steps are the same as step 2 of Example 1;

[0047] 3. The synthesis of pyridoxal phosphate, the steps are as follows:

[0048] In a 100mL three-necked reaction flask equipped with a stirrer and a thermometer, 3.7g (10.1mmol) of the pyridoxal phosphate Schiff base prepared in step 2 was added to 20.2mL of 2mol / L sodium hydroxide solution, and the temperature was raised to 35.0 Reaction at ℃ for 2.0h. After cooling to room temperature, the reaction solution was extracted twice with ethyl acetate and then separated (25.0 ml×2). 12.8 g of strong acid cation exchange resin was added to the water phase, stirred for 1.0 h, filtered with suction, and finally lyophilized with a lyophilizer to obtain 1.7 g of pyridox...

Embodiment 3

[0050] The specific steps for the synthesis of pyridoxal phosphate are as follows:

[0051] 1. Synthesis of pyridoxal hydrochloride Schiff base, the specific steps are the same as step 1 of Example 1;

[0052] 2. For the synthesis of pyridoxal phosphate Schiff base, the specific steps are the same as step 2 of Example 1;

[0053] 3. The synthesis of pyridoxal phosphate, the steps are as follows:

[0054] In a 500mL three-necked reaction flask equipped with a stirrer and a thermometer, 36.6g (100.0mmol) of pyridoxal phosphate Schiff base was added to 200.0mL of 2mol / L sodium hydroxide solution, and the temperature was raised to 35.0°C for 2.0h. After cooling to room temperature, the reaction solution was extracted twice with ethyl acetate and then separated (250.0 ml×2). Add 110.0 g of strong acid cation exchange resin to the water phase, stir for 1.0 h, filter with suction, and finally freeze-dry with a freeze dryer to obtain 16.8 g of pyridoxal phosphate as a white solid. It was de...

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Abstract

The invention provides a preparation method of pyridoxal 5-phosphate monohydrate. The preparation method comprises the following steps: 1, first oxidizing pyridoxine hydrochloride to pyridoxal hydrochloride, adding sodium sulfide, then dropwise adding p-ethoxyaniline to the solution, and carrying out a reaction to produce a pyridoxal hydrochloride Schiff base; 2, adding polyphosphoric acid to thepyridoxal hydrochloride Schiff base, performing a stirring reaction, first hydrolyzing polyphosphoric acid and then performing neutralization with an alkali solution to precipitate a large amount of an orange-red solid after the reaction is completed, and filtering and washing the solid to obtain a pyridoxal 5-phosphate Schiff base; and 3, hydrolyzing the pyridoxal 5-phosphate Schiff base with a 2mol / L of alkali solution, adding an organic solvent for extracting and performing liquid separation, adding a strong acid cation exchange resin into the aqueous phase, performing stirring for 1.0 h and then performing vacuum filtration, and performing freeze drying on the filtrate to obtain pyridoxal 5-phosphate monohydrate. The preparation method of pyridoxal 5-phosphate monohydrate is simple inoperation, mild in reaction conditions, relatively high in purity and yield of the final product, and suitable for industrial application, and has relatively good economic benefits.

Description

Technical field [0001] The invention relates to a preparation method of pyridoxal phosphate, and belongs to the technical field of pharmaceutical intermediate processing. Background technique [0002] Pyridoxal5-phosphatemonohydrate (Pyridoxal5-phosphatemonohydrate) Chemical name: (3-hydroxy-2-methyl-5-[(phosphoryloxy)methyl]-4-pyridinecarboxaldehyde. Pyridoxal phosphate is in pyridoxal An important substance is not only the coenzyme of transaminase and decarboxylase in amino acid metabolism, but also promotes the decarboxylation of glutamic acid and promotes the production of γ-aminobutyric acid. Pyridoxal phosphate is used in the synthesis of β-carbonyl amide drugs and biological activity research It is also used in a large number of fields, such as clinically used to treat Parkinson's syndrome, to promote transaminase to carry out transamination and increase the content of dopamine in the body. [0003] At present, although there are many methods for synthesizing pyridoxal phos...

Claims

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Application Information

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IPC IPC(8): C07F9/58
Inventor 尹传奇宣良明胡旭冯权武
Owner WUHAN INSTITUTE OF TECHNOLOGY
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