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Stable isotope labeling Clenproperol compound and synthesis method thereof

A technology of stable isotope and synthesis method, which is applied in the field of stable isotope-labeled Clempro compound and its synthesis

Inactive Publication Date: 2016-09-28
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, there are few public documents on the synthesis route of stable isotope-labeled crompprole, and there is no domestic literature report. Based on the principle of molecular design, we use stable isotope-labeled 2,6-dichloroaniline as a raw material, and undergo acylation, bromination, Stable isotope-labeled cromppro from four-step reaction of isopropylamination and reduction

Method used

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  • Stable isotope labeling Clenproperol compound and synthesis method thereof
  • Stable isotope labeling Clenproperol compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0157] A stable isotope labeled cromppro-D 2 The preparation method comprises the following steps:

[0158] 1. Stable isotope labeling 3,5-dichloro-4-aminoacetophenone-D 2 preparation of

[0159] Add 16.5g 2,6-dichloroaniline-D in a 250mL three-necked flask 3 , add 50mL of dichloromethane and stir to disperse, then add 27g of aluminum trichloride, add 11.8g of acetyl chloride dropwise under temperature control at 0°C, after the dropwise addition, raise the temperature and reflux to react for 4 hours, after acidification, filter with suction and wash with water to obtain 17.3g of light yellow 3,5-dichloro-4-aminoacetophenone-D 2 , yield 85.1%, HPLC detection, purity 99.5%; mass spectrometry detection, abundance 99.5atom%D.

[0160] 2. Stable isotope labeling of 3,5-dichloro-4-amino-α-bromoacetophenone-D 2 preparation of

[0161] Add 10.1g of 3,5-dichloro-4-aminoacetophenone-D into a 100mL three-neck flask 2 , add 20mL deuterated chloroform, copper bromide 22.5g, heat up ...

Embodiment 2

[0167] A stable isotope labeled cromppro-D 1 The preparation method comprises the following steps:

[0168] 1, Preparation of 3,5-dichloro-4-aminoacetophenone

[0169] Add 8.3g of 2,6-dichloroaniline to a 250mL three-neck flask, add 50mL of chloroform and stir to disperse, add 30g of ferric chloride, add 8.8g of acetyl chloride dropwise at a temperature of 0°C, and react at room temperature for 6 hours, after acidification, suction filtration and water washing to obtain 9.0 g of light yellow 3,5-dichloro-4-aminoacetophenone with a yield of 88.6%, and a purity of 99.5% by HPLC detection.

[0170] 2. Preparation of 3,5-dichloro-4-amino-α-bromoacetophenone

[0171] Add 5.1g of 3,5-dichloro-4-aminoacetophenone into a 100mL three-neck flask, add 20mL of chloroform, add 10g of liquid bromine dropwise, react at room temperature for 3 hours after the addition, stop the reaction, neutralize, and recover the solvent after washing with water 6.7 g of a light yellow solid was obtained,...

Embodiment 3

[0177] A stable isotope labeled cromppro-D 7 The preparation method comprises the following steps:

[0178] 1, Preparation of 3,5-dichloro-4-aminoacetophenone

[0179] Add 16.2g of 2,6-dichloroaniline into a 250mL three-neck flask, add 50mL of chloroform and stir to disperse, then add 20g of boron trifluoride, add 15.3g of acetyl chloride dropwise at 0°C, and react at room temperature for 3 After acidification, suction filtration and water washing gave 17.7g of light yellow 3,5-dichloro-4-aminoacetophenone with a yield of 86.9%. The purity was 99.5% by HPLC detection.

[0180] 2. Preparation of 3,5-dichloro-4-amino-α-bromoacetophenone

[0181] Add 10.2g of 3,5-dichloro-4-aminoacetophenone into a 100mL three-neck flask, add 20mL of dichloromethane, add 15g of NBS, react at room temperature for 5 hours after the addition, stop the reaction, and recover the solvent after washing with water to obtain 13.6g Pale yellow solid, yield 96.3%, HPLC detection, purity 99.0%.

[0182] ...

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Abstract

The invention relates to a stable isotope labeling Clenproperol compound and a synthesis method thereof. The method comprises the following steps of (1) using stable isotope labeling 2,6-dichloroaniline as raw materials to generate stable isotope labeling 3,5-dichloro-4-aminoacetophenone through Friedel-Crafts acyl reaction; (2) performing bromination on the stable isotope labeling 3,5-dichloro-4-aminoacetophenone to obtain stable isotope labeling 3,5-dichloro-4-amino-alpha-bromo acetophenone; (3) enabling the stable isotope labeling 3,5-dichloro-4-amino-alpha-bromo acetophenone and isopropylamine to take a reaction for obtaining stable isotope labeling 1-(4-amino-3,5-dichlone)-2-isopropyl amino ethyl ketone; (4) enabling the stable isotope labeling 1-(4-amino-3,5-dichlone)-2-isopropyl amino ethyl ketone and a reducing agent to take a reaction to generate stable isotope labeling Clenproperol. The stable isotope labeling Clenproperol compound and the synthesis method have the advantages that the process route is simple; the synthesis is easy; the stable isotope atom utilization rate is high; the obtained product can be easily separated and purified; the chemical purity and the fractional isotopic abudance are 99 percent or higher; the trace detection requirements in the food safety field can be sufficiently met.

Description

technical field [0001] The invention relates to the field of food safety, in particular to a stable isotope-labeled clenpro compound and a synthesis method thereof. Background technique [0002] Clenpro is a β2 adrenergic receptor agonist, mainly used to prevent and treat bronchial asthma and spasm in humans and animals. When they are used in livestock feeding at an amount 5-10 times higher than the therapeutic dose, they will have a significant nutritional "redistribution effect" - promote protein deposition in the animal body, promote fat decomposition and inhibit fat deposition, and can significantly improve the lean meat of the carcass Ratio, weight gain and feed conversion rate improvement, so it has been used as a growth promoter and feed additive for cattle, sheep, poultry, pigs and other livestock and poultry. However, this substance is highly harmful to the human body, causing symptoms of poisoning such as palpitations, headaches, dizziness, nausea, vomiting, fever...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/68C07C213/00
CPCC07C215/68C07B2200/05C07C213/00C07C221/00C07C225/22
Inventor 徐仲杰罗勇孙凯杨维成孙雯李美华涂亚辉钟佳琪方超
Owner SHANGHAI RES INST OF CHEM IND
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