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A kind of preparation method of 5-aminolevulinic acid hydrochloride

A technology of aminolevulinic acid hydrochloride and benzamidolevulinic acid, which is applied in the field of preparation of 5-aminolevulinic acid hydrochloride, can solve the problems of long synthetic route, easy operation and high proportion , to achieve the effects of high product yield and purity, convenient source of raw materials, and simple reaction operation

Active Publication Date: 2019-12-13
TAIZHOU VOCATIONAL & TECHN COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The disadvantage of this route is: the synthesis route is longer, the yield is lower (total yield: 21.6%), and there is a problem of high-pressure hydrogenation, which is not conducive to safe production
[0009] Advantages and disadvantages of this route: This route has relatively large defects. First, in the process of synthesizing 5-bromolevulinic acid, there is the generation of by-product 3-bromolevulinic acid, and the ratio is quite high, and it is difficult to Separation is not suitable for industrial production; the second is that the explosive reagent sodium azide is used in this route, which is easy to bring danger in operation, and it is more difficult to realize large-scale industrial production
[0012] Advantages and disadvantages of this route: This route has a higher yield, but the organic zinc and triphenylphosphine palladium chloride reagents used in the process generally need to be prepared in advance and the raw materials are expensive. Thionyl chloride is used in the acyl chloride process, and corrosion Larger, easy to cause pollution

Method used

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  • A kind of preparation method of 5-aminolevulinic acid hydrochloride
  • A kind of preparation method of 5-aminolevulinic acid hydrochloride
  • A kind of preparation method of 5-aminolevulinic acid hydrochloride

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Effect test

Embodiment 1

[0033] Add 10g (133mmol) of glycine and 100mL of 10wt% NaOH solution in the reaction flask, then start to lower the temperature to cool the system temperature to 15°C; add 21.6ml (186mmol) of benzoyl chloride, and then stir the reaction at room temperature for 0.5 h, after the reaction is over, add crushed ice 100g, then add concentrated hydrochloric acid dropwise for acidification to adjust the pH value = 2-3, so that a large amount of solids are precipitated, filtered and dried to obtain 23g of the corresponding benzoylglycine, the yield 96%.

Embodiment 2

[0035] Get and adopt the raw material benzoylglycine 5g (27.9mmol) synthesized in the above-mentioned embodiment 1 to add in the reaction flask, then add succinic anhydride 19.55g (195.34mmol, 7eq), triethylamine 6.06g (60mmol), DMAP (4g ) and pyridine 25ml, pyridine can be used as an organic base and directly as a solvent, then the temperature is raised to control the temperature at 45°C-50°C to carry out the Dakin-West reaction for 1h, after the reaction, add 200ml of 10wt% Na 2 CO 3 aqueous solution, continue to stir for 30min. Cooling, basification with 20wt% sodium hydroxide solution in an ice-water bath until the pH of the system is 9-10, then adding ethyl acetate to extract twice (each time using 50mL ethyl acetate to extract), collect the corresponding Then add concentrated hydrochloric acid to the water phase to acidify to pH=2, so that a large amount of solids are precipitated, filtered, and dried to obtain 5.2 g of the product benzamido-levulinic acid, with a yield...

Embodiment 3

[0038] Get and adopt the raw material benzoylglycine 5g (27.9mmol) synthesized in the above-mentioned embodiment 1 to add in the reaction flask, then add succinic anhydride 30g (167.4mmol), triethylamine 6.06g (60mmol), DMAP (4.5g) and Pyrrole 30ml, pyrrole can be used as an organic base or directly as a solvent, then the temperature is raised to control the temperature at 60°C and the Dakin-West reaction is carried out for 1.5h. After the reaction is completed, add 200ml of 10wt% NaHCO 3 aqueous solution, continue to stir for 30min. Cooling, alkalization to system pH value of 9-10 with 15wt% potassium hydroxide solution under ice-water bath, then, adding dichloromethane to extract twice (using 50mL dichloromethane to extract each time), collect the corresponding Aqueous phase, then adding mass concentration in the aqueous phase is 30% hydrochloric acid solution to carry out acidification to pH=2, make to precipitate a large amount of solid, filter, dry, obtain product benzami...

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Abstract

The invention relates to a preparation method of 5-aminolevulinic acid hydrochloride, belonging to the technical field of drug intermediate synthesis. In order to solve the problems of long route and great pollution at present, the invention provides the preparation method of the 5-aminolevulinic acid hydrochloride. The preparation method is characterized in that the method comprise the following steps of under the existence of organic alkali and DMAP, enabling benzoyl glycine to react with butanedioic anhydride by using Dakin-West to obtain benzoyl aminolevulinic acid; under the existence of hydrochloric acid, enabling the benzoyl aminolevulinic acid to be subjected to hydrolysis reaction to obtain the 5-aminolevulinic acid hydrochloride. The synthetic method has the advantages that the reaction route is short, the raw materials are convenient to obtain, the cost is low, the reaction operation is simple and convenient and the pollution is less, and the method has the effects of high product yield and high purity.

Description

technical field [0001] The invention relates to a preparation method of 5-aminolevulinic acid hydrochloride, belonging to the technical field of pharmaceutical intermediate synthesis. Background technique [0002] 5-Aminolevulinic acid hydrochloride (ALA) is an indispensable precursor for the synthesis of heme and chlorophyll in organisms, and has broad application prospects in the field of medicine. Not only can it be used to treat acne, rheumatoid arthritis, skin diseases and other diseases, but it can also be used as a new generation of photodynamic drugs in the treatment of brain tumors and skin cancers. [0003] At present, the existing synthetic methods of 5-aminolevulinic acid hydrochloride mainly contain the following synthetic routes: [0004] For example, Liu Hailing et al. (International Online Chemical Journal, 2005, 7(3):24) reported that succinic anhydride was used as a raw material to react 5-aminolevulinic acid through 5 steps such as monoesterification and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/04C07C229/22
CPCC07C227/04C07C231/02C07C231/12C07C229/22C07C233/83
Inventor 蒋军荣杨伟强徐峰柯中炉
Owner TAIZHOU VOCATIONAL & TECHN COLLEGE
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