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Synthetic method of commercialized 7-alkyne-4-oxygen-caprylic acid

A synthetic method, octanoic acid technology, applied in the field of synthesis of chemical probes, to achieve broad market prospects, save synthesis costs, and easy storage

Pending Publication Date: 2022-02-01
西安康福诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems existing in the existing alkyne-diaziridine-octanoic acid, the present invention provides a synthetic method of 7-alkyne-4-oxo-octanoic acid with low cost, simple route, yield and purity in line with commercialization, greatly Cost savings in the synthesis of commercial alkyne-diaziridine-carboxylic acids

Method used

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  • Synthetic method of commercialized 7-alkyne-4-oxygen-caprylic acid
  • Synthetic method of commercialized 7-alkyne-4-oxygen-caprylic acid
  • Synthetic method of commercialized 7-alkyne-4-oxygen-caprylic acid

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Embodiment 1

[0019]

[0020] 1. Add 415mg (2.17mmol) of cuprous iodide and 57mg (2.39mmol) of magnesium chips into a three-necked flask, and add 2mL of dry tetrahydrofuran, cool down to 0°C while stirring, and then slowly add 500mg (2.17mmol) of formula 1 Shown (4-bromo-1-butyne)-trimethylsilane, gradually warming up to room temperature after the addition is completed, stirring the reaction at room temperature for 2 hours to make the reaction complete, quenching the reaction with 110mg (0.44mmol) iodine, and finally using di After extraction with methyl chloride, the organic phase was spin-dried to obtain 458.96 mg (2.12 mmol) of the compound of formula 2, with a yield of 91.79%.

[0021] 2. After 433mg (2mmol) of the compound of formula 2 was dissolved in 2mL of tetrahydrofuran, it was added dropwise to 2mL of 240mg (2.4mmol) of succinic anhydride and 76.18mg (0.4mmol) of cuprous iodide under stirring conditions at -20°C. In tetrahydrofuran, after the addition, the temperature was rais...

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Abstract

The invention discloses a synthetic method of commercialized 7-alkyne-4-oxygen-octanoic acid, the method comprises the following steps: reacting (4-bromo-1-butyne)-trimethylsilane serving as a raw material with magnesium metal to generate a Grignard reagent, performing nucleophilic addition reaction with succinic anhydride, and finally performing hydrolysis reaction under an alkaline condition to generate the 7-alkyne-4-oxygen-octanoic acid. The whole synthetic route is short, the yield is high, the prepared 7-alkyn-4-oxygen-octanoic acid is stable and easy to store, and the synthetic cost of commercialized alkyne-bis (aziridine-carboxylic acid) is greatly saved as an important intermediate of alkyne-bis (aziridine-carboxylic acid).

Description

technical field [0001] The invention belongs to the technical field of synthesis of chemical probes, and in particular relates to a synthesis method of commercial 7-alkyne-4-oxo-octanoic acid. Background technique [0002] Alkyne-diaziridine-carboxylic acid is a kind of chemical probe. In biology and genetics, this kind of chemical probe can trace functional groups through protein activity. Usually, this type of chemical probe is used to pharmacologically identify new targets to discover therapeutic drugs. There are some protein functional groups, which are very complex and difficult to characterize. This requires the characterization of a series of protein evaluation ligands based on the emergence of new ligands, and alkyne-diaziridine-carboxylic acid is one of the important ones, which can Characterize this series of functional groups. In 2021, a patent was discovered that alkyne-diaziridine-carboxylic acid can be used to synthesize a drug that can treat parasitic trypan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/083C07C59/76C07F7/08
CPCC07C51/083C07F7/0803C07F7/083C07C59/76
Inventor 高浩杨原
Owner 西安康福诺生物科技有限公司