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Method for preparing high-content nemadectin

A technology of protecting group and oxo generation, which is applied in the field of preparing high-content nemoctine, and can solve the problem of low content of nemoctine products

Active Publication Date: 2017-06-13
内蒙古佳瑞米精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the problem of low content of nemoctine products existing in the prior art, the present invention provides a method for preparing high-content nemoctine, which has the advantages of simple post-treatment, few times of column separation and high content of nemoctine Advanced merit

Method used

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  • Method for preparing high-content nemadectin
  • Method for preparing high-content nemadectin
  • Method for preparing high-content nemadectin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The technical process of present embodiment preparation high-content nemoctine is as follows:

[0034]

[0035] (1) Reduction reaction:

[0036] Add 4.0g of 5-oxo(4-nitrobenzoyl)-23-oxonimoxetine (5.0mmol, 1.0eq, HPLC purity 95.0A%, white powder) into a 100mL three-necked flask, add 40.0g of methanol and stir After uniformity, a milky white suspension was obtained, put it into an ice-water bath and cool to 0~5°C, add 567mg (15.0mmol, 3.0eq) of sodium borohydride in batches, keep stirring for 1.0h after the addition, and pour the reaction solution into 40.0g of water , extracted twice with 40.0 g of dichloroethane, and the obtained oil layer was evaporated under negative pressure to remove the solvent to obtain 4.0 g (4.9 mmol, HPLC purity 94.0A%).

[0037] (2) Deprotection reaction:

[0038] 4.0g (4.9mmol, 1.0eq) of 5-oxo(4-nitrobenzoyl)-nimoctine obtained in step (1) was mixed with dichloroethane (20.0g) and methanol (20.0g) After dissolving, transfer it to a 10...

Embodiment 2

[0042]The technical process of present embodiment preparation high-content nemoctine is as follows:

[0043]

[0044] (1) Reduction reaction:

[0045] Add 8.1g of 5-oxo(4-chlorophenoxyacetyl)-23-oxonimoxetine (10.0mmol, 1.0eq, HPLC purity 96.2A%, white powder) into a 250mL three-necked flask, add methanol 81.0g Stir evenly to obtain a milky white suspension, put it in an ice-water bath to cool to 0~5°C, add 1135mg (30.0mmol, 3.0eq) of sodium borohydride in batches, keep stirring for 1.0h after the addition, and pour the reaction solution into 80.0g In water, extracted twice with 80.0 g of dichloroethane, and the obtained oil layer was vacuum-rotated to remove the solvent to obtain light yellow 5-oxo(4-chlorophenoxyacetyl)-nimoctine 8.0 g (9.8 mmol, HPLC purity 96.0A%).

[0046] (2) Deprotection reaction:

[0047] 8.0g (9.8mmol, 1.0eq) of the above-mentioned 5-oxo(4-chlorophenoxyacetyl)-Nimoctine was dissolved in 40.0g dichloroethane and 40.0g methanol, then transferred t...

Embodiment 3

[0051] The technical process of present embodiment preparation high-content nemoctine is as follows:

[0052]

[0053] (1) Deoxime reaction:

[0054] Add 4.0g (4.9mmol, 1.0eq, HPLC purity 97.02A%, white powder) of 5-oxo(4-nitrobenzoyl)-23-methoximoxine to a 100mL three-necked flask, add dioxane 40.0g dissolved clear, then added 3.6g hydrochloric acid (9.9g, 97.6mmol, 20.0eq, content 36wt.%), then heated to 50°C and kept stirring for 10.0h. The reaction solution was poured into 40.0g of water, extracted twice with 40.0g of dichloroethane, and the obtained oil layer was rotated to dryness under negative pressure to obtain light yellow 5-oxo(protecting group)-23-oxonimoxetin 3.8g (4.8mmol, HPLC purity 96.5A%, yield 98.0%).

[0055] (2) The reduction reaction, deprotection reaction and silica gel column separation process were the same as in Example 1, and finally 2.8 g of nimoctine (HPLC purity 96.5A%, content 93.7 wt.%, white solid) was obtained.

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Abstract

The invention discloses a method for preparing high-content nemadectin and belongs to the technical field of organic chemistry. The method comprises the following steps: taking crystallized and purified 5-oxygen (protecting group)-23-oxo nemadectin as a raw material, and then reducing, de-protecting and separating with a silica gel column, thereby acquiring the high-content nemadectin. The HPLC purity of the acquired nemadectin is more than or equal to 95.0A% and the content is more than or equal to 93.0wt%. The method has the advantages of simple post-processing, few column separation times and high content of nemadectin.

Description

technical field [0001] The invention relates to the technical field of preparation of nemoctine in organic chemistry, in particular to a method for preparing high-content nemoctine. Background technique [0002] Nemadectin is a sixteen-membered macrolide antibiotic produced by fermentation of Streptomyces blue gray (J.Chem.Soc., Chem.Commun., 1987, (6), 402-404) , is an antiparasitic drug. Nimoctine is further chemically modified by introducing a methyloxime group (=N-OCH 3 ) can obtain a more active insecticide, Moxidectin, which is currently widely used in veterinary clinics. It is a broad-spectrum, high-efficiency, new type of macrolide anthelmintic antibiotic. [0003] During the fermentation process, Streptomyces couscous produces not only nemoctine, but also various structural analogues, which are not easy to remove. At present, the main method to prepare high-content nemoctine is to separate and purify through multiple column separations of different types of macro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22
CPCY02P20/55C07D493/22
Inventor 戴耀李贺先刘玲玲赵宇航王荣良
Owner 内蒙古佳瑞米精细化工有限公司
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