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Synthesization method of stable isotope labeling beta receptor agonist

A stable isotope and synthesis method technology, applied in the field of synthesis of stable isotope-labeled β-receptor agonists, can solve the problems of difficult control of isotope abundance, low utilization rate of isotope atoms, long reaction steps, etc., and achieve high atom utilization rate , economy and use value are good, and the effect of short reaction time

Inactive Publication Date: 2017-03-29
SHANGHAI RES INST OF CHEM IND
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Problems solved by technology

Chinese patent CN102796013.A discloses a synthesis method of deuterium-labeled albuterol and its derivatives, but the reaction process involves high-temperature and high-pressure reduction, complicated operation, and the reduction process requires palladium carbon as a catalyst, which is expensive and has abundant isotopes. Degree control is difficult
Chinese patent CN201410663833.6 discloses a synthesis method of a stable isotope-labeled β-receptor agonist, but the patent uses bromoketone and tert-butylamine to aminate first, and then reduce it with a reducing agent to obtain a stable isotope-labeled β-receptor agonist agent, the reaction steps are long, the reaction time is long, the utilization rate of isotope atoms in the two-step reaction is low, and strong alkali sodium hydroxide and potassium hydroxide are used as catalysts, which easily cause abundance dilution

Method used

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  • Synthesization method of stable isotope labeling beta receptor agonist
  • Synthesization method of stable isotope labeling beta receptor agonist
  • Synthesization method of stable isotope labeling beta receptor agonist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A stable isotope labeled clenbuterol- 13 Synthesis of C

[0053] Add 4.12g of 3,5-dichloro-4-aminobromophenethyl alcohol into a 35mL reaction bottle, stir and dissolve 20mL of dichloromethane, then add tert-butylamine- 13 C 1.5g, triethylamine 2g, closed system, microwave power 50 watts, pressure 50psi; reaction temperature 40°C, reaction time 5min, after the reaction was completed, washed with water, dried to obtain 5.04g clenbuterol- 13 C, the yield is based on tert-butylamine- 13 C 90.8%, HPLC detection, purity 99.5%; mass spectrometry detection, abundance 99.5atom% 13 c.

Embodiment 2

[0055] A stable isotope labeled tobuterol- 13 C 3 Synthesis

[0056] Add 9.42g of o-chlorobromophenylethanol to the 80mL reaction bottle, stir and dissolve 45mL of chloroform, then add tert-butylamine- 13 C 3 3.0g, 3.5g sodium bicarbonate, closed system, set the microwave power to 100 watts, and the pressure to 20psi; the reaction temperature was 50°C, and the reaction time was 4min. After the reaction was completed, it was washed with water and dried to obtain 8.34g tobuterol- 13 C 3 , yield in terms of tert-butylamine- 13 C 3 Total 90.4%, HPLC detection, purity 99.2%; mass spectrometry detection, abundance 99.4atom% 13 c.

Embodiment 3

[0058] A stable isotope labeled brobuterol- 13 C 3 Synthesis

[0059] Add 7.44g of 3,5-dichloro-4-aminobromophenethyl alcohol into a 35mL reaction bottle, stir and dissolve 20mL of tetrahydrofuran, then add tert-butylamine- 13 C 3 1.6g, sodium carbonate 1.1g, closed system, set the microwave power to 40 watts, and the pressure to 35psi; the reaction temperature was 65°C, and the reaction time was 3min. After the reaction was completed, it was washed with water and dried to obtain 6.73g of brobuterol- 13 C 3 , yield in terms of tert-butylamine- 13 C 3 Total 91.2%, HPLC detection, purity 99.8%; mass spectrometry detection, abundance 99.5atom% 13 c.

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Abstract

The invention relates to a synthesization method of a stable isotope labeling beta receptor agonist. Through the organic synthesization method, stable isotope labeling tert-butylamine serves as a labeling precursor and reacts with a bromo-phenethyl alcohol compound in a microwave condition to generate the stable isotope labeling beta receptor agonist. Compared with the prior art, the synthesization method of the stable isotope labeling beta receptor agonist is simple, safe and reliable, and the product reaches 99% or above in chemical purity and isotope abundance after being simply separated and purified, and can fully meet requirements of beta receptor agonist detection of illegal additives in the food safety field.

Description

technical field [0001] The present invention relates to a synthesis method of beta receptor agonist, in particular to a synthesis method of stable isotope labeled beta receptor agonist. Background technique [0002] With the continuous improvement of human living standards, people's demand for animal-derived foods such as meat, eggs, and milk is increasing year by year. Especially in the past 30 years, veterinary drugs (including feed drug additives) have been widely used in animal husbandry, and the resulting problem of veterinary drug residues in food has gradually become a social focus that people generally pay attention to. In particular, frequent food safety incidents in recent years have not only caused great harm to the health and safety of the general public, but also caused dissatisfaction and distrust of government management, bringing a lot of unrest to society. At present, the illegal use of prohibited drugs, abuse of antibacterial drugs and drug additives, etc....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C215/68C07C215/30C07C269/06C07C271/44C07C213/00C07C215/60C07C253/30C07C255/59
CPCC07C213/02C07B2200/05C07C213/00C07C253/30C07C269/06C07C215/68C07C215/30C07C271/44C07C215/60C07C255/59
Inventor 徐仲杰钟佳琪罗勇涂亚辉孙雯盛立彦杨维成方超王浩然
Owner SHANGHAI RES INST OF CHEM IND
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