Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 5-aminolevulinic acid hydrochloride

A technique for the synthesis of aminolevulinic acid hydrochloride and its synthesis method, which is applied in the field of synthesis of drugs and drug intermediates, can solve the problems of expensive raw materials, easy pollution, long synthesis route, etc., and achieve high product yield, convenient operation, Quality Controlled Effects

Pending Publication Date: 2021-11-05
SHANDONG WEIGAO PHARM CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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
[0009] The disadvantage of this route is: the synthetic route is longer, the yield is lower (total yield: 21.6%), and there is a high-pressure hydrogenation problem, which is not conducive to safe production
[0012] Disadvantages of this route: There are relatively large defects in this route. First, in the process of synthesizing 5-bromolevulinic acid, there is a by-product 3-bromolevulinic acid, and the ratio is quite high, and it is difficult to carry out 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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 5-aminolevulinic acid hydrochloride
  • Preparation method of 5-aminolevulinic acid hydrochloride
  • Preparation method of 5-aminolevulinic acid hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A preparation method of 5-aminolevulinic acid hydrochloride, comprising the following steps:

[0045] (1) Preparation of 2-(3-chloro-2-oxypropyl) dimethyl malonate

[0046] Add 16.51 g of 1,3-dichloroacetone and 100 ml of methanol into a 500 ml three-necked flask, and stir magnetically. 13.21g of dimethyl malonate and 20ml of triethylamine dissolved in 50ml of methanol were slowly added dropwise to the 1,3-dichloroacetone solution, and the drop was completed in half an hour. Stir at room temperature for 4h. After concentrating under reduced pressure to dryness, add 100ml of dichloromethane, wash with purified water 3 times, each time with 50ml of water, and concentrate under reduced pressure to obtain 20.50g of colorless liquid (intermediate I). The yield of this step is 92%, and the purity is 96%. .

[0047] (2) Preparation of dimethyl 2-(3-(1,3-dioxoisoindol-2-yl)-2-oxopropyl)malonate

[0048] Add 11.13g of intermediate I, 12.03g of potassium imide phthalate and 8...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of 5-aminolevulinic acid hydrochloride, the method comprises the following steps: taking 1, 3-dichloroacetone as an initial raw material, reacting with a malonate compound, then carrying out ammonification reaction and hydrolysis decarboxylation, and finally decolorizing, concentrating and recrystallizing to obtain the 5-aminolevulinic acid hydrochloride. The method is high in yield, convenient to operate, stable in quality and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis of medicines and medicine intermediates, in particular to a preparation method of 5-aminolevulinic acid hydrochloride. Background technique [0002] 5-Aminolevulinic acid hydrochloride 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 method for synthesizing 5-aminolevulinic acid hydrochloride mainly contains the following routes: [0004] For example, Wang JJ et al. (Tetrahedron Lett, 1997, 38(5): 739-740) used glycine as a raw material to obtain 5-aminolevulinic acid hydrochloride through phthalimidization, acyl chloride, condensation and hydrolysis. [...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C227/04C07C229/22C07C67/343C07C69/716C07C227/08C07C229/24C07D209/48C07D487/18
CPCC07C67/343C07C227/08C07C227/18C07C227/04C07D209/48C07D487/18C07C69/716C07C229/24C07C229/22
Inventor 王智军王云鹏刘攀王帅军李晨光
Owner SHANDONG WEIGAO PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com