Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A

Methylorinic acid A was successfully synthesized through a series of compound reactions, which solved the problems of low extract content and unsatisfactory efficacy in natural medicines, and achieved large-scale production of this compound.

CN103772189BActive Publication Date: 2015-05-27SHANDONG LONGCHEN PHARM CO LTD
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Patent Information

Application Number
CN201410032181.6
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2014-01-23
Publication Date
2015-05-27
Estimated Expiration
2034-01-23

AI Technical Summary

Technical Problem

In the existing technology, the content of the stearic acid compound extracted from natural medicines is low, difficult to produce on a large scale, and has problems with unsatisfactory efficacy or toxic side effects, and there is a lack of effective synthesis methods.

Method used

Through a series of compound reactions, including esterification, reduction, substitution, alkylation, ester hydrolysis, decarboxylation, dehydration cyclization, condensation, oxidative cleavage, condensation, coupling, and ester hydrolysis, methylsuccinic acid was successfully synthesized. A.

Benefits of technology

Starting from simple and easily available raw materials, we achieved the large-scale synthesis of methylsuccinic acid A through a total of 13 steps of reaction, and realized its large-scale production and application.

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Abstract

The invention discloses a synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A. The synthesis method comprises the steps: esterifying a compound with a formula (I) to generate a compound with a formula (II); reducing the compound with the formula (II) to generate a compound with a formula (III); carrying out substitution on the compound with the formula (III) to generate a compound with a formula (IV); carrying out substitution on the compound with the formula (IV) to generate a compound with a formula (V); carrying out alkylation on the compound with the formula (V) to generate a compound with a formula (VI); carrying out esterolysis on the compound with the formula (VI) to generate a compound with a formula (VII); carrying out decarboxylation on the compound with the formula (VII) to generate a compound with a formula (VIII); carrying out dehydration cyclization on the compound with the formula (VIII) to generate a compound with a formula (IX); carrying out condensation on the compound with the formula (IX) to generate a compound with a formula (X); carrying out five-membered ring breakage on the compound with the formula (X) to generate a compound with a formula (XI); carrying out condensation on the compound with the formula (XI) to generate a compound with a formula (XII); carrying out coupling on the compound with the formula (XII) to generate a compound with a formula (XIII); carrying out esterolysis on the compound with the formula (XIII) to generate a compound with a formula (XIV), namely methyl pigeon pea ketonic acid A.
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