Synthetic method for carbonyl steroid-containing compound derivatization reagent

A technology of derivatization reagents and synthesis methods, applied in the direction of steroids, androstane derivatives, chemical instruments and methods, etc., can solve the problems of poor stability and low sensitivity of derivatized products, and achieve improved detection sensitivity, The effect of low cost and fast production

Inactive Publication Date: 2020-12-25
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention solves the technical problems of poor stability and low sensitivity of derivatization products of derivatization reagents containing carbonyl steroidal compounds in the prior art

Method used

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  • Synthetic method for carbonyl steroid-containing compound derivatization reagent
  • Synthetic method for carbonyl steroid-containing compound derivatization reagent
  • Synthetic method for carbonyl steroid-containing compound derivatization reagent

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Embodiment 1

[0026] The synthesis method of the carbonyl-containing steroid compound derivatization reagent of the present invention. Add N-hydroxyphthalimide (2.01g, 12.3mmol), DMF (30mL), 1,3-dibromopropane (2.5mL, 24.5mmol) and triethylamine (3.3 mL, 23.7mmol), stirred at 25°C for 16h. Diluted with water and extracted with ethyl acetate, the organic phase was dried, filtered and then column chromatographed (petroleum ether / ethyl acetate=5 / 1) to obtain a white solid 2-(3-bromopropoxy)isoindoline- 1,3-diketone 2.3g, yield 66%. Add 2-(3-bromopropoxy)isoindoline-1,3-dione (2.3g, 8.10mmol) and trimethylamine tetrahydrofuran solution (24mL, 24mmol) into a 48mL sealed tube and stir at 40°C for 12h , trimethylamine is dissolved in tetrahydrofuran THF inside. The solid was collected by filtration and washed with dichloromethane to give a white solid 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N,N-trimethylpropyl Ammonium bromide 2.36g, the yield is 85%. Add 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N...

Embodiment 2

[0028]The synthesis method of the carbonyl-containing steroid compound derivatization reagent of the present invention. Add N-hydroxyphthalimide (2.01g, 12.3mmol), DMSO (30mL), 1,3-dibromopropane (2.5mL, 24.5mmol) and triethylamine (3.3 mL, 23.7mmol), stirred at 20°C for 16h. Diluted with water and extracted with ethyl acetate, the organic phase was dried, filtered and then column chromatographed (petroleum ether / ethyl acetate=5 / 1) to obtain a white solid 2-(3-bromopropoxy)isoindoline- 1,3-diketone 2.3g, yield 66%. Add 2-(3-bromopropoxy)isoindoline-1,3-dione (2.3g, 8.10mmol) and trimethylamine tetrahydrofuran solution (24mL, 24mmol) into a 48mL sealed tube and stir at 35°C for 10h . The solid was collected by filtration and washed with dichloromethane to give a white solid 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N,N-trimethylpropyl Ammonium bromide 2.36g, the yield is 85%. Add 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N,N-trimethylpropylammonium bromide ((2.36g , 6.88mmol), TH...

Embodiment 3

[0030] The synthesis method of the carbonyl-containing steroid compound derivatization reagent of the present invention. Add N-hydroxyphthalimide (2.01g, 12.3mmol), DMF (30mL), 1,3-dibromopropane (2.5mL, 24.5mmol) and triethylamine (3.3 mL, 23.7mmol), stirred at 30°C for 16h. Diluted with water and extracted with ethyl acetate, the organic phase was dried, filtered and then column chromatographed (petroleum ether / ethyl acetate=5 / 1) to obtain a white solid 2-(3-bromopropoxy)isoindoline- 1,3-diketone 2.3g, yield 66%. Add 2-(3-bromopropoxy)isoindoline-1,3-dione (2.3g, 8.10mmol) and trimethylamine tetrahydrofuran solution (24mL, 24mmol) into a 48mL sealed tube and stir at 50°C for 20h . The solid was collected by filtration and washed with dichloromethane to give a white solid 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N,N-trimethylpropyl Ammonium bromide 2.36g, the yield is 85%. Add 3-((1,3-dioxo-2-isoindolinyl)-oxyl)-N,N,N-trimethylpropylammonium bromide ((2.36g , 6.88mmol), Me...

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Abstract

The invention relates to a synthetic method for a carbonyl steroid-containing compound derivatization reagent, and belongs to the technical field of chemical synthesis. The synthesis method comprisesthe following steps of: firstly, reacting 1, 3-dibromopropane with N-hydroxyphthalimide to synthesize 2- (3-bromopropoxy) isoindoline -1, 3-diketone; preparing 3-((1,3-dioxo-2-isoindolyl)-oxy)-N, N, N-trimethylpropylammonium bromide by utilizing 2-(3-bromopropoxy) isoindoline -1, 3-diketone; and finally, carrying out hydrazinolysis on the 3-((1, 3-dioxo-2-isoindoline)-oxy)-N, N, N-trimethylpropylammonium bromide. The synthesis method is low in cost, simple in step and high in yield; the carbonyl-containing steroid compound can be derivatized; a permanently charged group N+Me3 is introduced into the carbonyl-containing steroid compound, and the detection sensitivity of the carbonyl-containing steroid compound in ESIMS/MS is improved.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and more specifically relates to a synthesis method for a derivatization reagent of a carbonyl-containing steroid compound. Background technique [0002] Carbonyl-containing steroids are a class of non-polar compounds that are secreted by the endocrine system and regulate metabolic processes, and have important physiological functions. Due to the low concentration of carbonyl-containing steroids in biological samples, poor ionization efficiency, and many isomers, their analysis is facing great challenges. At present, the analysis of such compounds often uses the strategy of derivatization, and the introduction of ionizable groups in the molecule can significantly improve its sensitivity. Commonly used derivatization reagents include dansyl chloride (DNS-Cl), picolinic acid (PA), 1-methylimidazole-2-sulfonyl chloride (MLDS), pyridine-3-sulfonyl chloride (PS), (3-dimethyl (aminophenyl)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/04C07D209/48C07J1/00G01N30/02
CPCC07C291/04C07D209/48C07J1/0003G01N30/02
Inventor 杜支凤杨成文陶建梅孙逸姜宏梁
Owner HUAZHONG UNIV OF SCI & TECH
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