A method for preparing androstane-3,6,17-trione (E,Z)-3-[O-(2-aminoethyl)]oxime hydrochloride

The synthesis of androstane-3,6,17-trione (E,Z)-3-[O-(2-aminoethyl)]oxime hydrochloride was optimized by a five-step convergence strategy, which solved the problems of lengthy and inefficient processes in the prior art and enabled efficient and simplified industrial production.

CN122080103APending Publication Date: 2026-05-26ZHAOKE PHARMA HEFEI
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHAOKE PHARMA HEFEI
Filing Date
2026-03-27
Publication Date
2026-05-26

AI Technical Summary

Technical Problem

The existing synthetic route for androstane-3,6,17-trione (E,Z)-3-[O-(2-aminoethyl)] oxime hydrochloride is lengthy, inefficient, has low yield, and a complex impurity spectrum, making it difficult to achieve industrial production.

Method used

A five-step convergence strategy was adopted, which involves the reaction of benzophenone oxime with 2-chloroethylamine hydrochloride, combined with sodium bromate and ruthenium(IV) oxide catalytic oxidation, to optimize hydrolysis and solvent extraction, simplify the operation process, and improve selectivity and yield.

Benefits of technology

It significantly improves synthesis efficiency and purity, simplifies the operation process, reduces production costs, meets the requirements of industrial production, and obtains target products with high yield and high purity.

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Abstract

This invention provides a method for preparing androstane-3,6,17-trione (E,Z)-3-[O-(2-aminoethyl)]oxime hydrochloride, comprising the following steps: benzophenone oxime reacts with 2-chloroethylamine hydrochloride in dimethyl sulfoxide, followed by acid-base adjustment, toluene extraction, hydrolysis with concentrated hydrochloric acid to remove the protecting group, and crystallization to obtain high-purity 2-aminoethylamine hydrochloride; androstane-3,6,17-triol is used as a raw material and oxidized under the catalysis of sodium bromate and ruthenium oxide (IV), quenched, separated, washed with water, and crystallized by solvent replacement with isopropanol to obtain androstane-3,6,17-trione; the 2-aminoethylamine hydrochloride solution is mixed and reacted with the trione in tetrahydrofuran solution at low temperature, followed by salting out, filtration, separation, washing with saturated brine and drying with magnesium sulfate, and purification by solvent replacement, water dissolution and concentration, and cooling crystallization to obtain the high-purity target product. This invention significantly improves the yield of the target product by optimizing reaction conditions, while achieving readily available raw materials, low cost, and industrialized production through traditional chemical reaction pathways.
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