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16[alpha],16[beta],17[beta]-tris-deuterium-1,4-androstenedione synthesis method

A synthesis method and technology of androstenedione, which is applied in the field of synthesis of internal standard 16α, 16β, 17β-trideuterium-1,4-androstenedione, can solve the cumbersome post-processing process, complex synthetic route, and difficult synthesis Complex products and other issues, to achieve the effects of stable yield, simple synthetic route, and cheap and easy-to-obtain reaction raw materials

Inactive Publication Date: 2017-07-14
SHANGHAI ANPEL SCI INSTR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, 17β-Boldenone-D 3 The synthetic route of the compound is complicated, the deuterium substitution rate is low, the synthetic product is complex, and the post-treatment process is cumbersome, resulting in high production costs. my country can only rely on foreign imports for such standard products.

Method used

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  • 16[alpha],16[beta],17[beta]-tris-deuterium-1,4-androstenedione synthesis method
  • 16[alpha],16[beta],17[beta]-tris-deuterium-1,4-androstenedione synthesis method

Examples

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Embodiment 1

[0029] This example provides a synthesis method of 16α, 16β, 17β-trideuterium-1,4-androstenedione, the synthesis method comprising the following steps:

[0030] (A1) 1,4-androstenedione and deuterated water are mixed in tetrahydrofuran, and heated to reflux for 24-30 hours under the catalysis of a catalytic amount of weakly basic salt (such as potassium carbonate, sodium carbonate); the 1 , the substance ratio of 4-androstenedione to deuterated water is 1:100 to 1:500 (such as 1:300), and the volume of tetrahydrofuran is 1 / 2 to 1 / 4 of the volume of deuterated water ( such as 1 / 3);

[0031] (A2) stop reflux, cool to room temperature, use ethyl acetate to extract the reflux reaction solution, and concentrate the extracted organic phase to obtain the intermediate product 16α, 16β-dideuterium-1,4-androstenedione;

[0032] (A3) The intermediate product is mixed with sodium borodeuteride in deuterated methanol, and reacted for 20-60 minutes under ice bath conditions at -10°C to 0°C...

Embodiment 2

[0038] A specific application example of Embodiment 1 of the present invention.

[0039] (1) Weigh 1.42g of 1,4-androstenedione into a three-necked flask, add a catalytic amount of potassium carbonate 50mg, measure 30mL of deuterated water with a purity of 99.9% and 10mL of tetrahydrofuran into the reaction solution, and heat After reflux for 24 hours, the reaction was stopped and cooled to room temperature;

[0040] (2) The reaction solution was extracted three times with 40 ml of ethyl acetate, and the organic phase was collected and evaporated with a rotary evaporator to obtain 1.28 g of white solid powder, and the reaction yield was 90%;

[0041] (3) Add the 1.28g white solid powder into the there-necked flask, weigh 207mg of sodium borodeuteride and put it into the there-necked flask, add 18mL of deuterated methanol as the reaction solvent, and place the there-necked flask under ice-bath conditions (0 ℃) reaction for 30 minutes;

[0042] (4) Stop the reaction, add 1mol / ...

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Abstract

The present invention relates to a 16[alpha],16[beta],17[beta]-tris-deuterium-1,4-androstenedione synthesis method, which comprises: (A1) mixing 1,4-androstenedione and deuterated water in a first solvent, and carrying out heating reflux under the catalytic effect of a weak alkaline salt; (A2) extracting the reflux reaction liquid, and concentrating the extracted organic phase to obtain an intermediate product 16[alpha],16[beta]-di-deuterium-1,4-androstenedione; (A3) mixing the intermediate product and sodium borodeuteride in a second solvent, and carrying out selective reduction under an ice bath condition; (A4) acidifying the reduction reaction liquid to achieve the pH value of less than or equal to 2; and (A5) extracting the acidified reduction reaction liquid, and separating the organic phase by using a column chromatography method to obtain the target product 16[alpha],16[beta],17[beta]-tris-deuterium-1,4-androstenedione. The synthesis method of the present invention has advantages of simple reaction route, high product purity, low cost, and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing an internal standard 16α, 16β, 17β-trideuterium-1,4-androstenedione. Background technique [0002] With the popularization of chromatographic detection, stable isotope-labeled standards have become the most ideal quantitative internal standards, with stable isotopes (such as 2 H. 13 C. 15 N. 18 O) as an internal standard, not only improves the reliability of the experimental data, but also improves the test sensitivity. 16α,16β,17β-Trideuterium-1,4-androstenedione, commonly known as 17β-Boldenone-D 3 ,use 2 H is a stable isotope, which is an extremely stable internal standard with strong signal and no interference. It is often used in the detection of veterinary drug residues. 17β-Boldenone-D is added to the sample to be analyzed 3 It can be used as an internal standard for detection. Currently, 17β-Boldenone-D 3 The complex synthetic route, low ...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07B59/00
CPCC07J1/0033C07B59/007C07B2200/05
Inventor 赵鹏陈武炼张驰中
Owner SHANGHAI ANPEL SCI INSTR
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