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Synthetic method of tulathromycin

A technology of tyramectin and a synthesis method, which is applied in the field of tyramectin synthesis, can solve the problems of danger, high price, long reaction time and the like, and achieves the effects of safe operation, low cost and energy saving

Active Publication Date: 2014-03-19
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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  • Synthetic method of tulathromycin

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Experimental program
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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. Take 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 to solution 2 containing 7.33g of ketone compound I dichloromethane solution, st...

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 , 85% yield.

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

Embodiment 3

[0037] S1. Dissolve 1.6g of N-chlorosuccinimide in 12ml of dichloromethane, cool to 0°C, add dropwise a solution of dichloromethane containing 0.9g of dimethyl sulfide to obtain solution 1, and cool solution 1 to -25 ℃ for later use. 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 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 5.2g of ketone compound I , yield 72%.

[0038] S2. Take 2.41g trimethylsulfonium iodide, add 25ml acetonitrile, add 0.6g 60% sodium hydride, stir for half an hour, dropwise add 7.33g ketone compound I Acetonitrile solution was stirred at 80°C for 1 hour. Obtain 7.23...

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Abstract

The invention relates to the field of organic synthetic chemistry and specifically relates to a synthetic method of tulathromycin. No Cbz (carbamazepine)-Cl protection is used in the synthetic method of tulathromycin, which is provided by the invention; no Pd / C-H2 system needs to be used for deprotection; therefore, the operation is safer; besides, the reaction does not need to be carried out at an ultralow temperature, so that the energy source is saved; moreover, dimethylsulfide generated in the reaction process can be recovered and reused, so that the cost is relatively low; the reaction only comprises three steps, which is simpler than that in the known documents.

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 (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. It belongs to the third generation of macrolide antibiotics. The antibiotic can 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 hydro...

Claims

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Application Information

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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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