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A kind of method for preparing aminolevulinic acid hydrochloride

A technology of aminolevulinic acid hydrochloride and acetyl group, which is applied in the field of preparation of aminolevulinic acid hydrochloride, and can solve the problems of restricting the application of 5-ALA and its derivatives, low yield, and expensive raw materials

Active Publication Date: 2021-05-18
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There are many problems in the existing methods reported in the literature, such as expensive raw materials, difficult separation and purification of intermediates, low yield, and incapable of large-scale production, which seriously restrict the application of 5-ALA and its derivatives

Method used

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  • A kind of method for preparing aminolevulinic acid hydrochloride
  • A kind of method for preparing aminolevulinic acid hydrochloride
  • A kind of method for preparing aminolevulinic acid hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of aminolevulinic acid hydrochloride:

[0039] (1) Preparation of Compound B

[0040] Dissolve Boc-glycine (175.2kg, 1000.0mol, 1eq) in 1750kg tetrahydrofuran at room temperature, stir to dissolve, add magnesium chloride (95.2kg, 1000mol, 1eq) and N,N'-carbonyldiimidazole (162.1kg, 1000mol, 1eq), then add monomethyl malonate potassium salt (156.2kg, 1000mol, 1eq) in batches, heat up to 45°C and reflux until the reaction is complete, concentrate to remove the solvent, add 875kg of water, and extract 2~ 4 times, the organic phase was washed with 875 kg of 10% sodium bicarbonate solution, the washed organic phase was heated to remove the solvent, and dried to obtain 208 kg of compound B with a yield of 90%.

[0041] (2) Preparation of Compound D

[0042] Compound B (90.78kg, 392.5mol, 1eq) was dissolved in 907kg of tetrahydrofuran, 102.77kg of potassium carbonate was added, ethyl bromoacetate (72.11kg, 431.8mol, 1.1eq) was added dropwise, and stirred until th...

Embodiment 2

[0048] Preparation of aminolevulinic acid hydrochloride:

[0049] (1) Preparation of Compound B

[0050]Dissolve Boc-glycine (175.2kg, 1000.0mol, 1eq) in 1401kg tetrahydrofuran at room temperature, stir to dissolve, add magnesium chloride (142.8kg, 1500mol, 1.5eq) and N,N'-carbonyldiimidazole (162.1kg, 1000mol , 1eq), then add monomethyl malonate potassium salt (156.2kg, 1000mol, 1eq) in batches, heat up to 45°C and reflux until the reaction is complete, concentrate to remove the solvent, add 875kg of water, and extract 2 ~4 times, the organic phase was washed with 875 kg of 10% sodium bicarbonate solution, the washed organic phase was heated to remove the solvent, and dried to obtain 209 kg of compound B with a yield of 91%.

[0051] (2) Preparation of Compound D

[0052] Compound B (90.78kg, 392.5mol, 1eq) was dissolved in 907kg of tetrahydrofuran, 226.95kg of potassium carbonate was added, ethyl bromoacetate (72.11kg, 431.8mol, 1.1eq) was added dropwise, and stirred until...

Embodiment 3

[0058] Preparation of aminolevulinic acid hydrochloride:

[0059] (1) Preparation of Compound B

[0060] Dissolve Boc-glycine (175.2kg, 1000.0mol, 1eq) in 1750kg tetrahydrofuran at room temperature, stir to dissolve, add magnesium chloride (95.2kg, 1000mol, 1eq) and N,N'-carbonyldiimidazole (162.1kg, 1000mol, 1eq), then add monomethyl malonate potassium salt (234.3kg, 1500mol, 1.5eq) in batches, heat up to 45°C and reflux until the reaction is complete, concentrate to remove the solvent, add 875kg of water, and extract 2 ~4 times, the organic phase was washed with 875 kg of 10% sodium bicarbonate solution, the washed organic phase was heated to remove the solvent, and dried to obtain 210 kg of compound B with a yield of 91.6%.

[0061] (2) Preparation of Compound D

[0062] Compound B (90.78kg, 392.5mol, 1eq) was dissolved in 907kg of tetrahydrofuran, 102.77kg of sodium carbonate was added, ethyl bromoacetate (72.11kg, 431.8mol, 1.1eq) was added dropwise, and stirred until t...

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Abstract

The invention discloses a method for preparing aminolevulinic acid hydrochloride, which belongs to the field of chemical synthesis. The present invention uses glycine derivatives as starting materials, and provides a brand-new synthesis route of aminolevulinic acid hydrochloride through four steps of condensation, substitution, deprotection and hydrolysis. The synthesis method has short route, simple operation and high yield. Suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing aminolevulinic acid hydrochloride. Background technique [0002] In the medical field, 5-aminolevulinic acid (5-ALA) and its ester derivatives are important photosensitive diagnostic reagents for photodynamic therapy, and can also be used in the clinical treatment of acne, actinic keratosis, and various skin diseases. Treatment; in the field of agriculture, it can be used as a plant growth regulator, pesticide and insecticide; in the field of cosmetics, it can treat acne and promote hair growth, etc. Therefore, 5-aminolevulinic acid (5-ALA) and its ester derivatives have good market demands and broad application prospects. [0003] There are many reports on the synthesis method of 5-ALA. Patent CN102649768 discloses the following route: [0004] [0005] Patent JP2005272360 reports a method for synthesizing 5-ALA with succinic anhydride as raw materia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C227/10C07C227/16C07C229/22
CPCC07C227/10C07C227/16C07C227/18C07C229/22Y02P20/55
Inventor 李楷亢兴龙应忠华高永田郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP