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Compound 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, preparation method and application thereof

A compound, benzyl halide technology, applied in the field of medicinal chemistry, can solve problems such as affecting the purity of drugs, affecting the efficacy of drugs, and toxic and side effects

Pending Publication Date: 2020-06-02
INCREASEPHARM TIANJIN INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Impurities in the drug directly affect the efficacy of the drug and may lead to toxic side effects
The presence of impurities not only affects the purity of the drug, but also brings non-therapeutic toxic side effects, which must be controlled

Method used

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  • Compound 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, preparation method and application thereof
  • Compound 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, preparation method and application thereof
  • Compound 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Example 1 Preparation and purification of 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone (compound of formula I) (1) Preparation of compound of formula I

[0041] Add 20g of the compound of formula II into a 500ml single-necked bottle, add 200ml of ethanol, 72g of potassium carbonate powder, and 55g of benzyl chloride in sequence, and stir the reaction at 80°C. After the completion of the reaction as detected by TLC, the temperature was lowered and suction filtered, and the filtrate was concentrated to dryness under reduced pressure at 45° C. to obtain a concentrate with a purity of 86.6%.

[0042] (2) purification of formula I compound

[0043] Dissolve 15g of the concentrate prepared in step (1) in 50ml of dichloromethane, add 25g of 200-300 mesh silica gel to mix the sample, use 200-300 mesh of 100g of silica gel to pack the column; elute with 500ml of petroleum ether, and then use 500ml of volume ratio 50:1 petroleum ether: ethyl acetate was used for elution, and fi...

Embodiment 2

[0047] Example 2 Preparation and purification of 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone (compound of formula I)

[0048] (1) Preparation of formula I compound

[0049] Add 20g of the compound of formula II into a 500ml single-necked bottle, add 200ml of methanol, 60g of sodium hydroxide powder, and 55g of benzyl chloride in sequence, and stir the reaction at 60°C. After the completion of the reaction as detected by TLC, the temperature was lowered and suction filtered, and the filtrate was concentrated to dryness at 45°C under reduced pressure to obtain a concentrate with a purity of 72.3%.

[0050] (2) purification of formula I compound

[0051] Dissolve 15g of the concentrate prepared in step (1) in 50ml of ethyl acetate, add 25g of 200-300 mesh silica gel to mix the sample, use 200-300 mesh of 60g of silica gel to pack the column; elute with 1L petroleum ether, and then use 1L volume ratio 50:1 petroleum ether: ethyl acetate was used for elution, and finally 1 L of...

Embodiment 3

[0052] Example 3 Application of 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone (compound of formula I) as a reference substance in the determination of impurity content of compound of formula III

[0053]

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PUM

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Abstract

The invention belongs to the field of medical chemistry, particularly relates to 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, a preparation method and application thereof, and provides a new compound, which has a chemical name of 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, wherein the new compound can be used as a reference substance for impurity detection in a terbutaline raw material or intermediate drug synthesis process, and the content percentage of the compound in an intermediate is not more than 1.0%.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to 1-(2-benzyl-3,5-bis(benzyloxy)phenyl)ethanone, a preparation method and application thereof. Background technique [0002] Chronic obstructive pulmonary disease (COPD) is a chronic bronchitis and / or emphysema characterized by airflow obstruction, a common chronic disease that can progress to cor pulmonale and respiratory failure, abnormal inflammation with noxious gases and particles The morbidity rate and case fatality rate are very high, and the global incidence rate over the age of 40 has been as high as 9% to 10%. [0003] Terbutaline, the chemical name is 5-(1-hydroxy-2-tert-butylaminoethyl)benzene-1,3-diol (CAS No. 23031-25-6, molecular formula C 12 h 19 NO 3 ), is a short-acting β2-receptor agonist COPD treatment drug developed by AstraZeneca. It is a clinically recommended drug for mild and moderate COPD patients. Butaline inhalation has lower dose-depend...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/68G01N30/02
CPCC07C49/84C07C45/68G01N30/02C07C213/00C07C209/68C07C213/08C07C215/60
Inventor 张保献胡杰闫东辉秦梦芝曹瑛
Owner INCREASEPHARM TIANJIN INST CO LTD
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