A kind of synthetic method of telamectin

A technology of telamectin and synthesis method, which is applied in the field of synthesis of telamectin, can solve problems such as danger, high price, and long reaction time, and achieve the effects of safe operation, low cost, and energy saving

Active Publication Date: 2016-04-06
GENIFARM LAB INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is expensive, Pd is easily poisoned, and H2 is also dangerous
Literature (Guo Qiang, Ma Shutao; Research on Synthetic Technology of Tyramycin; Master's Degree Thesis of Shandong University) reported the use of acetic anhydride to protect the hydroxyl group, but this step needs to add acetic anhydride in batches, and the reaction time is long (>20 hours)

Method used

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  • A kind of synthetic method of telamectin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] S1. Dissolve 1.3g of N-chlorosuccinimide in 10ml of toluene, cool to 0°C, add dropwise a toluene solution containing 0.6g of dimethyl sulfide to obtain solution 1, and cool solution 1 to -25°C for later use. Dissolve 7.3g of azithromycin A in 25ml of toluene, add 0.5g of lithium hydroxide, stir at 25°C for 1 hour, then add dropwise to the above-mentioned mixed solution of N-chlorosuccinimide and dimethyl sulfide, keep React at -25°C for 2 hours, add dropwise a toluene solution containing 1g of triethylamine, return to room temperature after the dropwise addition, add dilute acid aqueous solution and stir, separate the organic phase, dry, filter, and recover the solvent to obtain 3.6g of ketone compound I. Yield 50%.

[0030] S2. Get 1.13g of trimethylsulfonium chloride, add 20ml of dichloromethane, add 0.56g of potassium hydroxide, stir for half an hour to obtain solution 2, add dropwise the dichloromethane solution containing 7.33g of ketone compound I in solution 2, ...

Embodiment 2

[0033] S1. Dissolve 2.6g of N-chlorosuccinimide in 20ml of toluene, cool to 0°C, add dropwise a toluene solution containing 2.5g of dimethyl sulfide to obtain solution 1, and cool solution 1 to -25°C for later use. Dissolve 7.3g of azithromycin A in 25ml of toluene, add 3.2g of lithium trifluoromethanesulfonate, stir at 25°C for 1 hour, then add dropwise to the reaction mixture of N-chlorosuccinimide and dimethyl sulfide , kept at -25°C for 2 hours, added dropwise a toluene solution containing 2g of triethylamine, returned to room temperature after the dropwise addition, added dilute acid aqueous solution and stirred, separated the organic phase, dried, filtered, and recovered the solvent to obtain 6.2g of ketone Compound I, yield 85%.

[0034] S2. Take 3.14g trimethylsulfonium bromide, add 25ml dichloroethane, add 2.4g sodium hydroxide, stir for half an hour to get solution 2, add dropwise dichloroethane containing 7.33g ketone compound I to solution 2 The solution was stirr...

Embodiment 3

[0037] S1. Dissolve 1.6g of N-chlorosuccinimide in 12ml of dichloromethane, cool to 0°C, add dropwise a solution of methylene chloride containing 0.9g of dimethyl sulfide to obtain solution 1, and cool solution 1 to -25°C spare. Dissolve 7.3g of azithromycin A in 25ml of dichloromethane, add 2.2g of calcium chloride, stir at 25°C for 1 hour, then add dropwise to the reaction mixture of N-chlorosuccinimide and dimethyl sulfide , kept at -25°C for 2 hours, added dropwise a toluene solution containing 1.2g triethylamine, returned to room temperature after the dropwise addition, added dilute acid aqueous solution and stirred, separated the organic phase, dried, filtered, and recovered the solvent to obtain 5.2g ketone Compound I, yield 72%.

[0038]S2. Take 2.41g of trimethylsulfonium iodide, add 25ml of acetonitrile, add 0.6g of 60% sodium hydride, stir for half an hour, add dropwise acetonitrile solution containing 7.33g of ketone compound I, and stir at 80°C for 1 hour. After...

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Abstract

The invention relates to the field of organic synthesis chemistry, in particular to a synthesis method of telamectin. The synthesis method of telamectin described in the present invention does not use Cbz-Cl protection, does not need to use Pd / C-H2 system to remove protection, and the operation is safer; and the reaction does not need to be carried out at ultra-low temperature, which saves energy more, and the reaction The dimethyl sulfide produced in the process can be recycled and reused, the cost is lower, and the reaction only needs 3 steps, which is simpler than the known literature.

Description

technical field [0001] The present invention relates to the field of organic synthetic chemistry, more specifically, relates to a synthetic method of telamectin. Background technique [0002] Tulathromycin (Tulathromycin, Formula Ⅰ), CAS No. 217500-96-4, is a new type of broad-spectrum antibacterial drug synthesized and developed by Pfizer Animal Health Products Company of the United States, belonging to the third generation of macrolide antibiotics. It selectively penetrates Gram-negative bacterial pathogens and was approved by EMEA in July 2002. In July 2005, the FDA approved Draxxin (10% Tyramectin Injection, Rui Kexin), a product of Pfizer Animal Health. In the 2008 Announcement No. 957, the Ministry of Agriculture of China allowed the use of telamectin in animal production for the first time. Macrolides generally only inhibit bacteria, but Tyramectin has both antibacterial and bactericidal effects. [0003] Azithromycin A (Formula II) contains a total of 5 hydroxyl g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/00C07H1/00
Inventor 王永东祝诗发黄志鹏操基元程稳
Owner GENIFARM LAB INC
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