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Process for synthesizing 5-aminovaleric acid hydrochloride

A technology of amino ketovalerate hydrochloride and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of low production cost, low yield, high price and the like, and achieves easy operation. , the raw materials are easily available, and the effect is conducive to industrial production

Active Publication Date: 2009-06-24
FUJIAN BOTE CHEM PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the yield of this method is too low (7%), and will use a large amount of expensive phthalimide potassium salts, its production cost is not low

Method used

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  • Process for synthesizing 5-aminovaleric acid hydrochloride
  • Process for synthesizing 5-aminovaleric acid hydrochloride
  • Process for synthesizing 5-aminovaleric acid hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] In a 500ml four-necked flask, add 300ml of methanol, 15g of sodium methoxide and 25g of methylene malonate. After stirring at room temperature for 15 minutes, add 45g of ethyl bromoacetoacetate dropwise. After concentration, the resulting solid was washed with water, dried in vacuo and used directly in the next step.

[0049] Dissolve the product in the previous step in 300ml of absolute ethanol, add 5g of p-toluenesulfonic acid, heat to reflux, concentrate after the TLC detection reaction, and the obtained product is directly used in the next step.

[0050] Dissolve the product in the previous step in 250ml of acetic acid, cool to 0°C, add dropwise a solution of 15g of sodium nitrite dissolved in 50ml of water, control the dropping speed so that the temperature does not exceed 5°C, after adding, add 100ml of water, and slowly heat up After the reaction, a large amount of solid was precipitated, filtered by suction, dried and used in the next step.

[0051]...

Embodiment 2

[0055]

[0056] In a 500ml four-necked flask, add 300ml of dimethyl sulfoxide, 15g of potassium carbonate and 25g of methylene malonate, stir at room temperature for 15 minutes, add 45g of ethyl bromoacetoacetate dropwise, and heat to 100 degrees to react After the reaction was detected by TLC, the reaction solution was poured into ice water, and a large amount of white solid was precipitated, which was directly used in the next step after vacuum drying.

[0057] Dissolve the product in the previous step in 300ml of anhydrous methanol, add 5g of p-toluenesulfonic acid, heat to reflux, concentrate after the TLC detection reaction, and the obtained product is directly used in the next step.

[0058] Dissolve the product in the previous step in 250ml of acetic acid, cool to 0°C, add dropwise a solution of 15g of sodium nitrite dissolved in 50ml of water, control the dropping speed so that the temperature does not exceed 5°C, after adding, add 100ml of water, and slowly heat up A...

Embodiment 3

[0062]

[0063] In a 500ml four-necked bottle, add 300ml of dimethylformamide, 18g of sodium acetate and 25g of isopropylidene malonate, stir at room temperature for 15 minutes, add 40g of ethyl chloroacetoacetate dropwise, and heat to 100 After the reaction was detected by TLC, it was poured into ice water, and a large amount of solid was precipitated, filtered by suction, dried in vacuum and used directly in the next step.

[0064] Dissolve the product from the previous step in 300ml of anhydrous methanol, add 5g of HCl, heat to reflux, concentrate after the TLC detection reaction, and the obtained product is directly used in the next step.

[0065] Dissolve the product in the previous step in 250ml of acetic acid, cool to 0°C, add dropwise a solution of 15g of sodium nitrite dissolved in 50ml of water, control the dropping speed so that the temperature does not exceed 5°C, after adding, add 100ml of water, and slowly heat up After the reaction, a large amount of solid wa...

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Abstract

The invention relates to an efficient novel method for synthesizing photosensitizing agent 5-ketoamine valerate hydrochloride. The method uses compounds of formula (I) and formula (II). In the formulas, R1 and R2 represent hydrogen or C1-C4 alkyl or substituted benzyl; R3 represents the C1-C4 alkyl or the substituted benzyl; and X represents Cl, Br, OTs and OMs. High purity 5-ketoamine valerate hydrochloride is prepared after alkylation reaction, interesterification, hydroxylamination, reduction and hydrolysis decarboxylation finally.

Description

Technical field: [0001] The invention relates to the field of synthesis of medical compounds, in particular to a synthesis method of 5-aminolevulinic acid hydrochloride. Background technique: [0002] Photodynamic therapy (PDT) was created in the 1970s. Due to the development and progress of photosensitive substances in recent years, it has gradually become one of the basic methods for treating tumors. 5-aminolevulinic acid hydrochloride is the hydrochloride salt of a new generation of photodynamic therapy drug 5-aminolevulinic acid (5-ALA), which is clinically used for actinic keratosis (Actinic Keratoses, AK) Treatment. [0003] Although the structure of 5-aminolevulinic acid hydrochloride is simple, its synthesis is quite difficult, especially the process for industrial production. The main synthetic methods can be summarized as: [0004] 1. Using glycine as raw material, phthalic amidation, acyl chloride, condensation, decarboxylation, hydrolysis (J.Chem.Soc.(1954, 18...

Claims

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Application Information

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IPC IPC(8): C07C229/22C07C227/12
Inventor 沈鑫廖立新林复兴何晓杨继东詹华杏
Owner FUJIAN BOTE CHEM PROD
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