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Synthesis method of stable isotope-labeled beta receptor agonist type compound

A stable isotope and agonist technology, applied in the field of preparation of isotope-labeled compounds, can solve the problems of high price, difficult isotope abundance control, complicated operation, etc., and achieve the effects of less by-products, good promotion prospects, and easy purification.

Active Publication Date: 2015-04-01
SHANGHAI RES INST OF CHEM IND
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Problems solved by technology

[0008] At present, there are few published documents on the synthesis route of stable isotope-labeled β-receptor agonist compounds. Chinese patent CN102796013.A discloses a synthesis method of deuterium-labeled albuterol and its derivatives, but there is no key intermediate in the experimental process. The synthesis method of stable isotope-labeled tert-butylamine involves high-temperature and high-pressure reduction during the reaction process, and the operation is complicated. The reduction process requires palladium carbon as a catalyst, which is expensive and difficult to control its isotope abundance.

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  • Synthesis method of stable isotope-labeled beta receptor agonist type compound
  • Synthesis method of stable isotope-labeled beta receptor agonist type compound
  • Synthesis method of stable isotope-labeled beta receptor agonist type compound

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preparation example Construction

[0040] A method for synthesizing stable isotope-labeled β-receptor agonist compounds, characterized in that the method adopts the following steps:

[0041] (1) Add acetone or stable isotope-labeled acetone dropwise to stable isotope-labeled methanol at low temperature, and control the molar ratio of stable isotope-labeled methanol to acetone or stable isotope-labeled acetone to be 1:0.5~1:3. React at room temperature for 0.5-24 hours, quench the reaction with dilute hydrochloric acid to obtain stable isotope-labeled tert-butanol, and then ammoniate with an ammoniating reagent to obtain stable isotope-labeled tert-butylamine;

[0042] (2) Bromoketones are used as the precursors of β-receptor agonist compounds, which undergo condensation reaction with stable isotope-labeled tert-butylamine in a liquid-phase environment, and are then reduced by a reducing agent to obtain stable isotope-labeled β-receptors Agonist compounds.

[0043] Step (1) When adding acetone or stable isotope...

Embodiment 1

[0065] A. Stable isotope labeled tert-butylamine-D 9 Synthesis

[0066] In a 100mL flask with a thermometer and a condenser tube, add 3.607g (0.1mol) of methanol -D 4 , lower the temperature to 0°C, and slowly add 38.071g (0.15mol) of iodine and an appropriate amount of red phosphorus in batches under stirring conditions. After the reaction is completed, distill the obtained iodomethane-D 3 , and then utilize the methyl iodide-D prepared above 3 Prepare Grignard reagent, slowly add 6.412g (0.1mol) acetone-D dropwise at -5°C 6 , react at room temperature for 0.5h, quench the reaction with dilute hydrochloric acid, and obtain tert-butanol-D 9 . After the obtained tert-butanol was purified by rectification, the reaction temperature was controlled at -10°C, and 7.059g (0.15mol) of methoxyamine was added dropwise to tert-butanol-D 9 Neutralize the catalyst, continue to react for 2 hours after the dropwise addition, and the reaction solution is rectified to obtain tert-butylami...

Embodiment 2

[0070] A. Stable isotope labeled tert-butylamine- 13 C 3 Synthesis

[0071] In a 100mL flask with a thermometer and a condenser tube, add 3.305g (0.1mol) of methanol- 13 C, lower the temperature to 0°C, and slowly add 38.071g (0.15mol) of iodine and an appropriate amount of red phosphorus in batches under stirring conditions. After the reaction is completed, distill the obtained methyl iodide- 13 C, and then utilize the methyl iodide prepared above- 13 C was prepared as Grignard reagent, and slowly added dropwise 6.081g (0.1mol) of acetone at 5°C- 13 C 2, react at room temperature for 3h, quench the reaction with dilute hydrochloric acid, and obtain tert-butanol- 13 C 3 . After the obtained tert-butanol was purified by rectification, the reaction temperature was controlled at -10°C, and 7.722g (0.15mol) of imine chloride was added dropwise to tert-butanol- 13 C 3 Neutralize the catalyst, continue to react for 2 hours after the dropwise addition, and the reaction solut...

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Abstract

The invention relates to a synthesis method of a stable isotope-labeled beta receptor agonist type compound. The synthesis method comprises the following steps: (1) by taking stable isotope-labeled methanol as a raw material, reacting with acetone or stable isotope-labeled acetone, and ammonifying to obtain stable isotope-labeled tert-butylamine; and (2) by taking a bromoketone type compound as a precursor of the beta receptor agonist type compound, reacting with stable isotope-labeled tert-butylamine to prepare the stable isotope-labeled beta receptor agonist type compound. Compared with the prior art, the method for preparing the stable isotope-labeled beta receptor agonist, provided by the invention, is simple, safe and reliable, the chemical purity of the product after separation and purification is above 99.0%, the isotopic abundance is above 98.0% atom, and the product can fully meet the requirements of residual detection in the field of food safety.

Description

technical field [0001] The invention relates to a preparation method of an isotope-labeled compound, in particular to a synthesis method of a stable isotope-labeled beta receptor agonist compound. Background technique [0002] With the development and progress of society and the continuous improvement of human living standards, the demand for animal-derived foods such as meat, eggs, and milk is increasing year by year. However, the current food safety is not optimistic, especially the safety of animal-derived food, which has become a global issue, and veterinary drug residues are the main reason for the decline in the safety of animal-derived food. With the long-term irrational use of veterinary drugs and pharmaceutical additives in the process of raising livestock and poultry, the veterinary drugs and their additives that remain in animals enter the human body along the food chain, posing a potential threat to human health. Therefore, strengthening the detection of veterin...

Claims

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Application Information

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IPC IPC(8): C07C215/68C07C215/60C07C215/30C07C213/00C07C213/02C07C255/59C07C253/30C07C271/44C07C269/00C07B59/00
Inventor 杨维成黄路敏罗勇杨超李美华孙雯潘洁宋家龙徐仲杰方超
Owner SHANGHAI RES INST OF CHEM IND
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