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Endo-(14s)-3-methoxy-17-methylmorphinan picrate and its preparation method and use

A technology of picric acid and compounds, applied in the field of compound synthesis, can solve problems such as inconvenient storage, unfavorable detection work, compound instability, etc.

Active Publication Date: 2017-02-15
APELOA PHARM CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the long-term commercial production process of dextromethorphan hydrobromide, a large amount of compound of formula (B) is required for quality inspection. However, the compound of formula (B) is unstable, inconvenient for storage, and not conducive to the testing work , so there is an urgent need to solve this practical problem in the production process

Method used

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  • Endo-(14s)-3-methoxy-17-methylmorphinan picrate and its preparation method and use
  • Endo-(14s)-3-methoxy-17-methylmorphinan picrate and its preparation method and use
  • Endo-(14s)-3-methoxy-17-methylmorphinan picrate and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] During the production process of dextromethorphan, 10.0 g of the mother liquor concentrate of dextromethorphan free base (wherein the HPLC content of the compound of formula B is 6.2%) was added to 25 ml of acetone for recrystallization, and 7.5 g of free base crude product was obtained by filtration, and the mother liquor was concentrated to dryness to obtain 2.4 g of oil (wherein the HPLC content of the compound of formula B is 24.1%). ——This embodiment is to enrich the content of the impurity formula (B) compound in the mother liquor.

Embodiment 2

[0047] Add 10 g of silica gel to the oil obtained in Example 1 and stir evenly, separate and purify by column chromatography, the eluent is (volume ratio): toluene: ethyl acetate: methanol: dichloromethane: ammonia water=55:20:13 :10:2. Sampling was monitored by TLC or HPLC to obtain a solution containing the compound of formula (B) as an impurity, which was concentrated to dryness to obtain 0.2 g of the compound of formula (B) as an oily substance.

[0048] Take 0.2g of the compound of impurity formula (B), dissolve it in 4ml of 95% ethanol, add dropwise a 10% ethanol solution of picric acid, a yellow solid precipitates, and filter until no solid precipitates to obtain a powdery solid, dry to constant Weight, 0.15g of the compound of formula (C) was obtained.

Embodiment 3

[0050] Take 0.15 g of the compound of formula (C) obtained in Example 2, dissolve it in 5 ml of ethanol-acetone (volume ratio 1:1) mixed solution, seal it up but leave gaps, let it stand at room temperature, and cultivate single crystals. Several days later, a single crystal of the compound of formula (C) was obtained, and the absolute stereo configuration was confirmed by single crystal diffraction analysis.

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Abstract

During the long-term commercial process for producing dextromethorphan hydrobromide, large amounts of endo-(14S)-3-methoxy-17-methylmorphinan are required for use in the aspects of quality control, however, endo-(14S)-3-methoxy-17-methylmorphinan is unstable, inconvenience for storage, and also goes against the execution of the testing procedure, and hence it is imperative to solve the practical problem generated in this production process in the art. In view of this, disclosed in the present invention is endo-(14S)-3-methoxy-17-methylmorphinan picrate in the form of a solid and a preparation method and use thereof, i.e. being used for detecting endo-(14S)-3-methoxy-17-methylmorphinan in the process for synthesizing dextromethorphan.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to endo-(14S)-3-methoxy-17-methylmorphinan picrate and its preparation method and application. Background technique [0002] The compound of formula (A), dextromethorphan hydrobromide, is a widely used oral antitussive. The compound of formula (B)-endo-(14S)-3-methoxy-17-methylmorphinan is an impurity produced during the synthesis of dextromethorphan hydrobromide. [0003] In the long-term commercial production process of dextromethorphan hydrobromide, a large amount of compound of formula (B) is required for quality inspection. However, the compound of formula (B) is unstable, inconvenient for storage, and not conducive to the testing work , so this field urgently needs to solve this practical problem that produces in the production process. Contents of the invention [0004] The present invention aims to solve the practical needs in the above-mentioned production process. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/28C07C205/24C07C201/12
CPCC07D221/28
Inventor 王宏博周后元应瑞芬舒理建
Owner APELOA PHARM CO LTD
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