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Phosphopyridoxal intermediates, preparation method of same, application of same, and method for preparing phosphopyridoxal therefrom

A technology of pyridoxal phosphate and intermediate, which is applied in the field of intermediate compound and preparation thereof, can solve the problems of difficult industrialized production, difficult source of raw materials, complicated steps and the like, and achieves the effects of simple operation, mild conditions and high reaction yield

Inactive Publication Date: 2012-11-07
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The technical problem to be solved by the present invention is to provide a simple, efficient and mild method for preparing pyridoxal phosphate in order to overcome the defects of complicated steps, difficult sources of raw materials and difficulty in applying to industrial production in the existing method for synthesizing pyridoxal phosphate. The intermediate of pyridoxal and its preparation method, and its application in the synthesis of pyridoxal phosphate and the method of synthesizing pyridoxal phosphate by it

Method used

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  • Phosphopyridoxal intermediates, preparation method of same, application of same, and method for preparing phosphopyridoxal therefrom
  • Phosphopyridoxal intermediates, preparation method of same, application of same, and method for preparing phosphopyridoxal therefrom
  • Phosphopyridoxal intermediates, preparation method of same, application of same, and method for preparing phosphopyridoxal therefrom

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1 N, the reaction of N'-diisopropylpropylenediamine and pyridoxal

[0035] In benzene (15ml), add pyridoxal (6.0mmol) and N, N'-diisopropylpropylenediamine (7.2mmol), heat up to 80°C for reflux and separate the produced water, continue the reaction until the thin layer Chromatography showed that the pyridoxal raw material disappeared, and the solvent was removed under reduced pressure, and ethyl acetate (10 ml) was recrystallized to obtain 1.39 g of the condensation product, with a yield of 75.5%.

[0036]

Embodiment 2

[0037] Embodiment 2 N, the reaction of N'-diethylpropylenediamine and pyridoxal

[0038] In toluene (15ml), add pyridoxal (6.0mmol) and N, N'-diethylpropylenediamine (9mmol), heat up to 110°C for reflux and separate the produced water, continue the reaction until thin layer chromatography It showed that the pyridoxal raw material disappeared, the solvent was removed under reduced pressure, and benzene (10 ml) was recrystallized to obtain 1.43 g of the condensation product, with a yield of 85.4%.

[0039]

Embodiment 3

[0040] Embodiment 3 N, the reaction of N'-dipropylpropylenediamine and pyridoxal

[0041] In xylene (20ml), add pyridoxal (6.0mmol) and N, N'-dipropylpropylenediamine (7.8mmol), heat up to 140°C for reflux and separate the produced water, continue the reaction until the thin layer Chromatography showed that the pyridoxal raw material disappeared, and the solvent was removed under reduced pressure, and the condensation product was recrystallized from toluene (15ml) to obtain 1.50g of the condensation product, with a yield of 81.4%.

[0042]

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Abstract

The invention discloses phosphopyridoxal intermediates shown in a formula I, wherein R1 and R2 are same or different alkyls. The invention also discloses a method for preparing the phosphopyridoxal intermediates, wherein in a non-polar solvent, pyridoxal and N, N'-disubstituted propane diamine are subjected to condensation reaction. The invention further discloses the application of the phosphopyridoxal intermediates in synthesizing phosphopyridoxal, and a method for preparing the phosphopyridoxal by the intermediates. According to the method for preparing the phosphopyridoxal by the intermediates, the phosphopyridoxal intermediates shown in the formula I, and polyphosphoric acid, or a mixture of P2O5 and phosphorous acid, or a mixture of P2O5 and a phosphorous acid water solution react to obtain pyridoxal polyphosphate protected by aldehyde groups. Then water is added into the pyridoxal polyphosphate to react to obtain the phosphopyridoxal. The methods for preparing the phosphopyridoxal intermediates and the phosphopyridoxal have the advantages of simple and convenient operation, mild conditions, higher yield, and higher purity.

Description

technical field [0001] The present invention relates to a class of intermediate compounds and their preparation methods and applications, in particular to a class of pyridoxal phosphate intermediates and their preparation methods and applications, as well as a method for preparing pyridoxal phosphate therefrom. Background technique [0002] Pyridoxal phosphate is a vitamin B 6 A derivative of vitamin B 6 An active form involved in many metabolic reactions of proteins, fats and carbohydrates. Pyridoxal phosphate is the coenzyme of transaminase and decarboxylase in amino acid metabolism, which can promote the decarboxylation of glutamic acid and the production of γ-aminobutyric acid. GABA is an inhibitory neurotransmitter. The coenzyme for all amino acid transaminases is pyridoxal phosphate. Through transamination, amino acid, carbohydrate and fat metabolism are linked; through decarboxylation, a variety of biologically active substances can be generated, such as histamine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07F9/6558C07F9/58
CPCY02P20/55
Inventor 卞红平周后元
Owner SHANGHAI INST OF PHARMA IND CO LTD
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