Preparation method of 6-deuterated dansyl chloride

A technology of dansyl chloride and deuteration, which is applied in the field of preparation of 6-deuterated dansyl chloride, can solve the problems of low yield and achieve the effects of less intermediate products, improved yield, high yield and high quality

Inactive Publication Date: 2020-12-01
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are 6 deuterated dansyl chloride derivatization reagents at present, but the original synthetic method has a low yield, only (60-70)%, and uses the highly toxic raw material deuterated dimethyl sulfate

Method used

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  • Preparation method of 6-deuterated dansyl chloride
  • Preparation method of 6-deuterated dansyl chloride
  • Preparation method of 6-deuterated dansyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Prepare the reaction materials according to the following proportions:

[0057] The mol ratio of sodium hydride and 5-amino-1-naphthalenesulfonic acid is 4.2:1;

[0058] The mol ratio of deuteroiodomethane and 5-amino-1-naphthalenesulfonic acid is 4.9:1;

[0059] The molar ratio of phosphorus oxychloride, phosphorus pentachloride and deuterated solid material is 1.75:0.29:1, and the specific process and dosage are as follows:

[0060] In the first step, suspend 448.4 mg (18.68 mmol) of sodium hydride solid in 1 mL of N,N-dimethylformamide, add 1 g (4.48 mmol) of 5-amino-1-naphthalenesulfonic acid, and cool to 0°C. Add 3.2g (22mmol) of CD 3 After 1, the temperature was raised to 35° C., and the reaction was carried out for 2 hours; water was added in an ice bath, and 6N HCl was added to adjust the pH of the solution to 3, and a solid was precipitated, filtered by suction, and dried at 120° C. for 2 hours to obtain a deuterated solid material;

[0061] In the second st...

Embodiment 2

[0064] Prepare 6 deuterated dansyl chlorides in the manner of Example 1, the difference is that the amount of raw materials and reaction conditions, wherein:

[0065] The mol ratio of sodium hydride and 5-amino-1-naphthalenesulfonic acid is 3.5:1;

[0066] The mol ratio of deuteroiodomethane and 5-amino-1-naphthalenesulfonic acid is 4.5:1;

[0067] The mol ratio of phosphorus oxychloride, phosphorus pentachloride and deuterated solid material is 2:0.3:1;

[0068] The temperature of the first substitution reaction was 37° C., and the reaction time was 1.5 h; the total yield was 73%, and the purity of the obtained target product was 73%.

Embodiment 3

[0070] Prepare 6 deuterated dansyl chlorides in the manner of Example 1, the difference is that the amount of raw materials and reaction conditions, wherein:

[0071] The mol ratio of sodium hydride and 5-amino-1-naphthalenesulfonic acid is 5:1;

[0072] The mol ratio of deuteroiodomethane and 5-amino-1-naphthalenesulfonic acid is 5.5:1;

[0073] The mol ratio of phosphorus oxychloride, phosphorus pentachloride and deuterated solid material is 1.8:0.35:1;

[0074] The temperature of the first substitution reaction is 30° C., the time is 2.5 h, the total yield is 82%, and the purity of the obtained target product is 80%.

[0075] As can be seen from the above examples, the method provided by the present invention can rapidly prepare 6-deuterated dansyl chloride, the reaction raw materials are easy to obtain, the preparation method is simple and easy to control, and the yield is high, reaching more than 75%; the overall reliability of the preparation method is high, and it is s...

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Abstract

The invention belongs to the technical field of isotope derivatization reagent preparation, and particularly relates to a preparation method of 6-deuterated dansyl chloride. According to the preparation method, 6-deuterated dansyl chloride can be prepared from reaction raw materials including 5-amino-1-naphthalene sulfonic acid, sodium hydride, deuterated methyl iodide, phosphorus oxychloride andphosphorus pentachloride. The preparation method has the advantages of easily available raw materials, low toxicity, few intermediate products and high yield.

Description

technical field [0001] The invention belongs to the technical field of isotope derivatization reagents, in particular to a preparation method of 6-deuterated dansyl chloride. Background technique [0002] In the study of metabolomics, small molecular compounds contained in biological samples can reflect the metabolic state of the body, and dansyl chloride can specifically bind to the active hydrogen atoms of small molecular compounds, thereby enhancing the mass spectrometric response of small molecular compounds. The combination of isotopic dansyl chloride derivatization reagents and dansyl chloride derivatization reagents has outstanding advantages in qualitative identification of metabolites and screening of unknown metabolites; the combination of deuterated dansyl chloride derivatization reagents with standard substances can be more convenient The obtained derivatized standard substance isotope standard is used to supplement co-elution and matrix effects in quantitative r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/88C07C303/18C07C303/44C07C309/47C07C303/22C07B59/00
CPCC07C303/18C07C303/44C07C303/22C07B59/001C07B2200/05
Inventor 再帕尔阿不力孜张瑞萍汪满江措王玉成张国宁臧清策贺玖明刘家兴
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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