Synthesis method of isotope labeled dansyl chloride-13C2

An isotope labeling, dansyl chloride technology, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of large consumption of sodium bicarbonate, large environmental impact, and material flushing, and achieve simplified post-processing, improved safety, and safe operation. handy effect

Inactive Publication Date: 2015-09-30
无锡贝塔医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The yield of route two is 75%, is an acceptable yield, but this method is to use a large amount of phosphorus oxychloride, and phosphorus oxychloride is highly toxic, and has a great impact on the environment, and after the reaction finishes During the quenching process, a large amount of sodium bicarbonate is consumed, a large amount of gas is generated, and it is easy to cause flushing

Method used

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  • Synthesis method of isotope labeled dansyl chloride-13C2
  • Synthesis method of isotope labeled dansyl chloride-13C2
  • Synthesis method of isotope labeled dansyl chloride-13C2

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example 1

[0025] Dissolve dansulphonic acid-13C2 (0.5g, 1.99mmol) in 20ml of anhydrous dichloromethane solvent, cool to 0°C under nitrogen protection, add dropwise anhydrous N,N-dimethylformamide (0.5ml, 22.56 mmol), stirred for 10 minutes, continued to dropwise add thionyl chloride (2ml, 27.54mmol), heated at 60°C for 4 hours after the dropwise addition; after the reaction, cooled the solution to room temperature, and added ice water while stirring the residue, And use sodium bicarbonate to adjust the pH value to 7, then extract twice with dichloromethane, combine all organic phases, use 10ml of dichloromethane each time, then wash with 5ml of water and 5ml of saturated brine successively, and wash the organic phase with 2 g of anhydrous magnesium sulfate was dried, filtered and concentrated to dryness to obtain 0.61 g of isotopically labeled dansyl chloride-13C2 crude product.

[0026] The isotope-labeled dansyl chloride-13C2 crude product obtained above was separated with a 400-mesh ...

Embodiment 2

[0029] Dissolve dansulphonic acid-13C2 (0.5g, 1.99mmol) in 20ml of anhydrous dichloromethane solvent, cool to 0°C under nitrogen protection, add dropwise anhydrous N,N-dimethylformamide (0.5ml, 22.56 mmol), stirred for 10 minutes, continued to add dropwise oxalyl chloride (2.4ml, 27.54mmol), heated at 60°C for 4 hours after the dropwise addition, after the reaction, cooled the solution to room temperature, and distilled off the solvent and chlorinated reagent under reduced pressure , add 10ml of ice water to the residue under stirring, adjust the pH value to 7 with sodium bicarbonate, extract the solution twice with diethyl ether, each time using 10ml of diethyl ether, combine all organic phases, then wash with 5ml of water and saturated with 5ml Wash with brine, dry the organic phase with 2 g of anhydrous magnesium sulfate, filter and concentrate to dryness to obtain 0.59 g of isotope-labeled dansyl chloride-13C2 crude product.

[0030] The isotope-labeled dansyl chloride-13C...

Embodiment 3

[0033]Dissolve dansulphonic acid-13C2 (0.5g, 1.99mmol) in 20ml of anhydrous tetrahydrofuran solvent, cool to 0°C under nitrogen protection, add dropwise anhydrous N,N-dimethylformamide (0.5ml, 22.56mmol) , stirred for 10 minutes, continued to add thionyl chloride (2ml, 27.54mmol) dropwise, and heated at 65°C for 4 hours after the dropwise addition was completed. After the reaction, the solution was cooled to room temperature, and the solvent and chlorinated reagent were distilled off under reduced pressure. 10ml of ice water was added to the residue under stirring, and the pH value was adjusted to 7 with sodium bicarbonate, and the solution was extracted twice with dichloromethane, using 10ml of dichloromethane each time, all organic phases were combined, and then washed with 5ml of water and Wash with 5 ml of saturated brine, dry the organic phase with 2 g of anhydrous magnesium sulfate, filter and concentrate to dryness to obtain 0.55 g of isotope-labeled dansyl chloride-13C2...

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Abstract

The invention relates to a synthesis method of isotope labeled dansyl chloride-13C2. The synthesis method is characterized by comprising the following steps: dissolving dansyl acid-13C2 in a solvent, cooling to 0 DEG C under nitrogen protection, dropwise adding anhydrous N,N-dimethylformamide and further dropwise adding a chlorination reagent; after the dropwise adding operation is finished, heating to the range of 30-70 DEG C and reacting for 2-5 hours; after the reaction is finished, cooling the solution to a room temperature, removing the solvent and the chlorination reagent by virtue of reduced-pressure distillation, adding ice water to the residue while stirring, and then adding sodium bicarbonate to regulate the pH value to the range of 5-7, extracting organic phases by use of dichloromethane or ether, mixing the organic phases, orderly washing by use of water and saturated salt water, drying the organic phase by use of anhydrous magnesium sulfate, and then filtering, concentrating and drying to obtain the crude product of the isotope labeled dansyl chloride-13C2. The synthesis method of the isotope labeled dansyl chloride-13C2 has the advantages of safe operation, good convenience and relatively high yield.

Description

technical field [0001] The invention relates to a method for synthesizing isotope-labeled dansyl chloride-13C2. Background technique [0002] Liquid chromatography coupled to mass spectrometry (LC / MS) has become a very important tool in metabolic research. An ideal LC / MS platform will identify and quantify all metabolites present in biological samples such as cell extracts and biological fluids. Unfortunately, it is very challenging to detect all metabolites at once due to the large differences in the chemophysical properties of the metabolites. [0003] One strategy to address this diversity is to divide metabolomes into groups based on hydrophobicity, chemical structure, or other attributes, and then use several tailor-made optimized LC / MS methods to target each metabolome. Group metabolites were analyzed. [0004] However, we can also look for an analysis strategy for selectively labeling metabolites based on the fact that the metabolites contain certain chemical funct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/47
Inventor 朱称古费静李刚
Owner 无锡贝塔医药科技有限公司
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