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Synthetic method of alkyl acid testosterone compound

A synthesis method and compound technology, applied in the synthesis field of alkyl acid testosterone compounds, can solve the problems of environmental pollution, toxicity, increase cost and the like, and achieve the effect of improving preparation efficiency

Inactive Publication Date: 2017-12-26
EVERLIGHT CHEMICAL INDUSTRIAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above synthetic method needs to use a large amount of pyridine as a solvent, which is toxic and easily causes environmental pollution. In addition, after the reaction, steps such as acid-base extraction and column chromatography are still required, resulting in time-consuming process and Disadvantages such as increased costs
[0004] In addition, Chinese patent CN103910777A also proposes a synthetic method for preparing testosterone derivatives, which also uses alcoholic hydroxy steroids as a starting material, and in the case of highly volatile chloroform (Chloroform) as a solvent, adding a dehydrating agent and Catalyst and alkanoic acid compounds undergo esterification reaction to form derivatives of testosterone alkanoate. After the reaction is completed, further acid-base extraction is still required for purification, so the overall process steps are tedious and time-consuming, and highly toxic chloroform is more suitable for environmental damage

Method used

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  • Synthetic method of alkyl acid testosterone compound
  • Synthetic method of alkyl acid testosterone compound
  • Synthetic method of alkyl acid testosterone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1-7 is to provide the detailed synthesis method of testosterone undecanoate (Testosterone undecanoate), is to use testosterone (Testosterone) as starting material to carry out esterification reaction, and this esterification reaction is as shown in the following formula program:

[0026]

[0027] First, under nitrogen, 5g of testosterone was thoroughly mixed with 25ml of N,N-dimethylformamide (DMF, solvent) and 5ml of pyridine (pyridine, base), and then 4.6ml of Undecanoylchloride (Undecanoylchloride), and react at room temperature for 1 hour, after the reaction, add 5ml of water and stir for 1 hour, the product precipitates and is filtered, and then rinses the product with acetone aqueous solution and then vacuum-dries it at room temperature , to obtain 7.6 g of testosterone undecylate, the yield was 96%, HPLC: 98.26%.

[0028] Next, the recrystallization step is to add 120g of testosterone undecylate into 480ml of acetone, stir until it is completely dis...

Embodiment 2

[0030] This example is roughly the same as Example 1, the difference lies in the types of solvents used and the steps of subsequent recrystallization are different. In this example, 25ml of N,N-dimethylacetamide was used as a solvent, and 7.6g of testosterone undecylate was obtained after the reaction, with a yield of 96%, HPLC: 99.40%.

[0031] Next, the recrystallization step of this embodiment is to add 6.1g of testosterone undecylate into 61ml of ethanol, stir until completely dissolved, stir in an ice bath for 1 hour, filter and rinse with ethanol, and The testosterone undecanoate obtained after recrystallization is Form S crystal.

Embodiment 3

[0033] First, 5 g of testosterone was thoroughly mixed with 50 ml of acetonitrile (solvent) and 1.7 ml of pyridine (pyridine, base) under nitrogen, and then 4.6 ml of undecanoyl chloride was added at 0-10° C. Under reaction for 5 hours, after the reaction ended, add 10ml of water and stir for 0.5 hours to separate out the product and filter, then rinse the product with acetone aqueous solution and vacuum-dry it at room temperature to obtain 5.5g of testosterone undecylate , the yield was 69%, HPLC: 98.80%.

[0034] Next, the recrystallization step is to add 3g of testosterone undecylate into 15ml of DMF, stir at 35°C until completely dissolved, then add 1ml of water and stir for 0.5 hours, filter and rinse with DMF aqueous solution Yes, the testosterone undecylate obtained after recrystallization is the S crystal form (Form S).

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Abstract

A method for synthesizing the testosterone alkylate compound, comprising performing esterification reaction on the testosterone compound in the presence of a solvent and a base to obtain the testosterone alkylate compound. In the synthesis method of the alkylate testosterone compound provided by the present invention, the solvent is a water-soluble organic solvent, so after the reaction is completed, the product can be directly precipitated by adding water, which simplifies the overall process steps.

Description

technical field [0001] The invention relates to a synthesis method of testosterone alkylate compound, in particular to a synthesis method which can simplify the preparation steps and improve the purity. Background technique [0002] Testosterone (testosterone, testosterone) is a male hormone drug, which can promote the development and maturation of male sexual organs and secondary sexual characteristics, and can resist estrogen, and promote protein and bone synthesis. Testosterone is used for the treatment of hypogonadism, supplementing the symptoms of insufficient self-secretion or inability to naturally secrete testosterone, so testosterone can be administered regularly to maintain the testosterone content in the blood. [0003] At present, most of the methods for preparing testosterone derivatives are synthesized by the acid chloride method, such as the synthesis method disclosed in the patent WO9967270A1, which uses alcoholic hydroxy steroids as a starting material, and ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 施雅芳蔡嘉忠姚启祥
Owner EVERLIGHT CHEMICAL INDUSTRIAL CORPORATION
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