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Preparation method of methyl tetraacetate compound

A compound, the technology of ethyl acetate, which is applied in the field of preparation of methyl tetraacetate compounds, can solve the problems of low yield and low purity, and achieve the effect of low temperature, high purity and high yield

Active Publication Date: 2021-09-03
NANJING CHIA TAI TIANQING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the preparation method of the compound of formula I recorded in the above literature is limited to the milligram-level production scale. When the scale-up production is carried out, there are many problems such as a rapid decrease in yield and low purity.

Method used

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  • Preparation method of methyl tetraacetate compound
  • Preparation method of methyl tetraacetate compound
  • Preparation method of methyl tetraacetate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1 prepares formula I compound according to the method disclosed in CN104177301B

[0054] Prepare the formula I compound according to the preparation method disclosed in Example 1.8 of CN104177301B, and only increase the feeding amount from the mg level to the g level, the details are as follows:

Embodiment 11

[0056] Add (S)-1,2-diaminopropane hydrochloride (5g), methyl bromoacetate (52.02g), and potassium carbonate (46.92g) into acetonitrile (340mL), react at 50°C for 4 hours, and the reaction ends , filtered off inorganic salts, concentrated the filtrate to dryness, added HCl (150mL, 12%) solution to acidify, washed with petroleum ether, adjusted the pH to 10 with saturated sodium carbonate solution, extracted with dichloromethane, dried and concentrated to dryness, The compound of formula I was obtained with a yield of 56%.

Embodiment 12

[0058]Add (S)-1,2-diaminopropane hydrochloride (10g), methyl bromoacetate (104.04g), and potassium carbonate (93.84g) into acetonitrile (680mL), react at 50°C for 4 hours, and the reaction ends , filtered off inorganic salts, concentrated the filtrate to dryness, added HCl (300mL, 12%) solution to acidify, washed with petroleum ether, adjusted pH to 10 with saturated sodium carbonate solution, extracted with dichloromethane, dried and concentrated to dryness, The compound of formula I was obtained with a yield of 31%.

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Abstract

The invention provides a preparation method of a methyl tetraacetate compound. By improving an existing milligram-grade process and through a phase transfer catalyst and a special salt-forming precipitation process, the yield and the purity of the product is increased and the preparation method is more suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a simple and efficient preparation method of methyl tetraacetate compounds. Background technique [0002] (S)-1,2-diaminopropane-methyl tetraacetate, the chemical structure is as shown in formula I, [0003] [0004] It is the key intermediate for the preparation of dexrazoxane (also known as dexrazoxane). Dexrazoxane is a lipophilic derivative of the chelating agent ethylenediaminetetraacetic acid. It is used as a chemical protective agent clinically, mainly for the prevention of anthracene Cyclic drug-induced cardiotoxicity. The mechanism of cardiotoxicity caused by anthracyclines is mainly due to the generation of reactive oxygen species during the formation of stable complexes between anthracyclines and iron, which cause lipid peroxidation to the myocardium and damage the myocardium. As a cardioprotective agent of chemotherapy drugs, dexrazoxane re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/08C07C229/16
CPCC07C227/08C07C229/16
Inventor 许健舒伟曹菁柴雨柱王华萍徐丹朱春霞
Owner NANJING CHIA TAI TIANQING PHARMA
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