N-substituted carbonyl fluorine sulfonamide compound as well as preparation method and application thereof

A carbonyl fluorosulfonamide and compound technology, which is applied in the preparation of sulfuric acid amide, organic chemistry, etc., can solve the problems of increased storage and use, no commercialization, and easy volatility, and achieves low toxicity, simple preparation, and wide substrate adaptability Effect

Active Publication Date: 2021-07-16
中宏鑫投资控股(深圳)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of sulfuryl fluoride to synthesize this series of compounds in the laboratory also has extremely obvious defects: the compound is a colorless liquid with strong corrosiveness, easy hydrolysis, and easy volatility, which adds great difficulty to storage and use. So despite having similar reactivity to chlorosulfonyl isocyanate, this reagent has not been commercially available

Method used

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  • N-substituted carbonyl fluorine sulfonamide compound as well as preparation method and application thereof
  • N-substituted carbonyl fluorine sulfonamide compound as well as preparation method and application thereof
  • N-substituted carbonyl fluorine sulfonamide compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193]

[0194] Dried N-hydroxysuccinimide (1.15g, 10mmol) was added to 10mL of ultra-dry methanol, stirred at 0°C, sodium methoxide (540mg, 10mmol) was added, and returned to room temperature. After two hours of reaction, the solvent was spin-dried, and the water was removed by azeotropic evaporation with toluene three times, and the residual solvent was drained by an oil pump. Add 20 mL of ultra-dry acetonitrile, stir at 0°C, add dropwise fluorosulfonyl isocyanate (0.8 mL, 10 mmol), return to room temperature, and react for 2 hours. Concentrate the solvent to about 5 mL, and add dropwise to 80 mL of vigorously stirred methyl A solid was precipitated from tert-butyl ether, filtered, washed with 5 mL of methyl tert-butyl ether, and the residual solvent was drained by an oil pump to obtain 2.2 g of a white solid with a yield of 85% and a decomposition temperature of 163.2°C. 1 H NMR (400MHz, CD 3 CN)δ2.70(s,4H); 13 C NMR (101MHz, CD 3 CN) δ172.1, 155.5, 26.2; 19 F NMR (3...

Embodiment 2

[0196]

[0197] Add dried N-hydroxysuccinimide (11.5 g, 100 mmol) into 100 mL of ultra-dry methanol, stir at 0°C, add potassium tert-butoxide (11.2 g, 100 mmol), and return to room temperature. After two hours of reaction, the solvent was spin-dried, and the water was removed by azeotropic evaporation with toluene three times, and the residual solvent was drained by an oil pump. Add 200mL of ultra-dry acetonitrile, stir at 0°C, add dropwise fluorosulfonyl isocyanate (8mL, 100mmol), return to room temperature, and react for 2h, concentrate the solvent to about 50mL, and add dropwise to 800mL of vigorously stirred methyl tert-methyl A solid was precipitated from butyl ether, filtered, washed with 50 mL of methyl tert-butyl ether, and the residual solvent was drained by an oil pump to obtain 24.5 g of a white solid with a yield of 87% and a decomposition temperature of 166.7°C. 1 H NMR (400MHz, DMSO) δ2.71 (s, 4H); 13 C NMR (101MHz, DMSO) δ171.2, 153.3, 25.3; 19 F NMR (376MH...

Embodiment 3

[0199]

[0200] Dried N-hydroxysuccinimide (391mg, 3.4mmol) was added to 5mL of ultra-dry methanol, stirred at 0°C, and tetramethylammonium hydroxide (wt.25% in methanol) (1.22g, 3.4mmol), returned to room temperature. After two hours of reaction, the solvent was spin-dried, and the water was removed by azeotropic evaporation with toluene three times, and the residual solvent was drained by an oil pump. Add 10 mL of ultra-dry acetonitrile, stir at 0°C, add dropwise fluorosulfonyl isocyanate (0.27 mL, 3.4 mmol), return to room temperature, and react for 2 hours. Concentrate the solvent to about 1 mL, and add dropwise to 10 mL of vigorously stirred formazan with a dropper. A solid was precipitated from methyl tert-butyl ether, filtered, washed with 3 mL of methyl tert-butyl ether, and the residual solvent was drained by an oil pump to obtain 1.7 g of a white solid with a yield of 80% and a decomposition temperature of 155.6°C. 1 H NMR (400MHz, CD 3 CN) δ3.08(s,12H),2.70(s,4...

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Abstract

The invention discloses an N-substituted carbonyl fluorine sulfonamide compound as well as a preparation method and application thereof. The N-substituted carbonyl fluorine sulfonamide compound comprises positive ions and negative ions, and the negative ions are shown in the formula I. The N-substituted carbonyl fluorine sulfonamide compound is low in toxicity, simple to prepare and convenient to use, is in a solid stable state at normal temperature, and reacts with a substrate to efficiently synthesize an N-amino carbonyl fluorine sulfonamide product; and besides, the compound is wide in substrate adaptability and can comprise primary amine and secondary amine compounds, so that the compound has important academic and application values.

Description

technical field [0001] The invention relates to an N-substituted carbonyl fluorosulfonamide compound, a preparation method and an application thereof. Background technique [0002] The hexavalent sulfur-fluorine functional group exhibits mild reaction conditions, high efficiency, insensitivity to oxygen and water, no metal catalysis, wide range of substrates and special properties of orthogonality, making it widely used in chemistry, biology and materials, etc. field. Since Professor K.Barry Sharpless and Jiajia Dong first proposed and successfully realized the hexavalent sulfur-fluorine exchange reaction in 2014 (Angew.Chem.Int.Ed.2014, 9430), this type of reaction has been used in organic synthesis chemistry, material chemistry , medicinal chemistry, chemical biology, especially the selective labeling and modification of protein molecules, etc., have attracted extensive attention and shown good application prospects. It is called a new generation of click chemistry, which...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/46C07D209/48C07C303/34C07C307/02C07D317/66C07D207/14C07D207/09C07D209/14C07D401/04C07D473/04C07D211/58C07D203/20C07D211/56
CPCC07D207/46C07D209/48C07C303/34C07C307/02C07D317/66C07D207/14C07D207/09C07D209/14C07D401/04C07D473/04C07D211/58C07D203/20C07D211/56C07C2603/42C07C2603/26
Inventor 董佳家孙守军
Owner 中宏鑫投资控股(深圳)有限公司
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