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Method for synthesizing spermidine hydrochloride

A technology of spermidine hydrochloride and compounds, which is applied in the field of synthesis of spermidine hydrochloride, can solve the problems of long synthesis route and low reaction yield, and achieve short synthesis steps, simple process conditions and mild reaction conditions Effect

Active Publication Date: 2020-06-19
南京康立瑞生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the current method for synthesizing spermidine, the general situation is that the synthetic route is relatively long, and more dangerous reducing agents such as lithium aluminum hydride are used, and even control reagents such as hydrazine hydrate are used, and the reaction yield is not high.

Method used

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  • Method for synthesizing spermidine hydrochloride
  • Method for synthesizing spermidine hydrochloride
  • Method for synthesizing spermidine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0035] (1) Under normal temperature conditions, sequentially add Boc-protected compound 2a (2.08g, 11mmol), Boc-protected propylenediamine (1.74g, 10mmol), triphenylphosphine (2.88g, 11mmol), and add 50ml of tetrahydrofuran to dissolve, Finally, diisopropyl azodicarboxylate (10 mmol) was added, stirred at room temperature for an hour, and the reaction was monitored by TLC until the reaction was completed.

[0036] (2) Add 10 mL of 4M hydrochloric acid solution to the above reaction system, TLC monitors until the reaction of compound 3 generated in the above (1) is complete, add 30 mL of water, extract with EA, collect the aqueous phase, continue to extract the organic phase with water for three times, and combine the water Mutually. The water was distilled off under reduced pressure to obtain the crude product of compound 4, and the crude product was crystallized and purified with methanol / dichloromethane system to extract compound 4.

Embodiment 2

[0038] (1) Under normal temperature conditions, sequentially add Boc-protected compound 2a (2.08g, 11mmol), Boc-protected propylenediamine (1.74g, 10mmol), triphenylphosphine (2.88g, 11mmol), and add 50ml of tetrahydrofuran to dissolve, Finally, diisopropyl azodicarboxylate (10 mmol) was added, stirred at room temperature for an hour, and the reaction was monitored by TLC until the reaction was completed.

[0039] (2) After the reaction, the solvent was distilled off under reduced pressure, and the compound 3 was obtained by column chromatography separation. The obtained compound 3 was dissolved in methanol, 10 mL of 4M hydrochloric acid solution was added, TLC monitored until the reaction was completed, the solvent and low boiling point compounds were removed under reduced pressure, and the obtained crude product was crystallized and purified by methanol / dichloromethane system to obtain compound 4.

[0040] The obtained target product was detected, and the results were as fol...

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Abstract

The invention relates to a method for synthesizing spermidine hydrochloride. The reaction formula is shown as the following formula (I) which is described in the specification. In the formula (I), theprotective group R1 of amino in 4-amino-1-butanol of a compound 2 is one of tert-butyloxycarboryl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl Mmt-, and a protective group R2 of propane diamine of the compound is one of tert-butyloxycarbonyl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl (Mmt-). A reagent used in the Mitsunobo reaction condition is one of triphenylphosphine, di-tert-butyl azodicarboxylate, diethyl azodicarboxylate and diisopropyl azodicarboxylate. The preparation method disclosed by the invention is simple in required process condition, mild in reaction condition, capable of effectively obtaining spermidine hydrochloride, relatively short in synthesis step and relatively high in synthesis yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis methodology, in particular to a method for synthesizing spermidine hydrochloride. Background technique [0002] Spermidine is a polyamine widely distributed in organisms, which can inhibit neuronal NO synthase, bind and precipitate DNA, and can also be used to purify DNA-binding proteins and stimulate T4 polynucleotide kinase activity. Spermidine can participate in many biological processes in organisms, such as regulating cell proliferation, cell aging, organ development, immunity and cancer and other physiological and pathological processes. On September 1, 2013, German and Austrian scientists jointly researched that spermidine may prevent the onset of Alzheimer's disease. The synthetic method of spermidine mainly has following several routes at present: [0003] [0004] In the current method for synthesizing spermidine, the general situation is that the synthetic route is relati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/14C07C209/62C07C209/84
CPCC07C209/62C07C209/84C07C269/06C07C211/14C07C271/20Y02P20/55
Inventor 吴荣
Owner 南京康立瑞生物科技有限公司
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