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Tulathromycin A synthesis method

The technology of a kind of telamycin, synthesis method, is applied in the synthetic field of telamycin A, can solve the problems such as long reaction time, many unsafe factors, large amount of catalyst palladium carbon, etc., achieve simple and safer operation, avoid adding Hydrogen reaction, effect of improving reaction efficiency

Active Publication Date: 2016-10-26
MASTEAM BIO TECH
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Problems solved by technology

[0005] Dimethyl sulfide is generated in the synthetic reaction process of epoxide (compound 2), and the existence of dimethyl sulfide can cause catalyst palladium carbon poisoning, and then make hydrogenation deprotection reaction speed very slow, and the consumption of catalyst palladium carbon is larger (the amount reaches about 50% of the raw material weight), the reaction time is too long (the deprotection time is about 4 days) is not conducive to reaction synthesis, precious metals are used as catalysts, the cost is high, and there are many unsafe factors in high-pressure reactions, which is not conducive to industrial production.

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Embodiment 1

[0035]Put 20 g of epoxide (compound 2), 80 g of isopropanol and 20 g of n-propylamine into a 250 mL three-necked flask, start stirring, and react at 20 °C after the dissolution is complete, and react at 20 °C for 48 h. Add 60 g of methylamino alcohol solution into the reaction flask, and react at 40°C for 24 h, and the reaction is monitored by HPLC. After the reaction finishes, all solvents and excess deprotection reagents are distilled off under reduced pressure, and 100 g of methyl tert-butyl ether is added to the residue, stirred and dissolved completely, and 6.1 g of trifluoroacetic acid and 60 g of methyl tert-butyl ether are added dropwise. The mixture was stirred for 4 h, filtered, and dried to obtain the trifluoroacetic acid salt of telamycin. Add 140 mL of dichloromethane to the trifluoroacetic acid salt, add potassium carbonate aqueous solution (potassium carbonate 8.93 g, water 140 mL) under stirring, and separate layers after stirring for 30 min, add 140 mL of dich...

Embodiment 2

[0037] Put 20 g of epoxide (compound 2), 80 g of n-butanol and 30 g of n-propylamine into a 250 mL three-necked flask, start stirring, and heat up the oil bath to the internal temperature of 40 °C after the dissolution is complete, and react at 40 °C for 24 h. Add 60 g of methylamine aqueous solution into the reaction bottle, and react at 40 °C for 24 h, and the reaction is monitored by HPLC. After the reaction was completed, all solvents and excess deprotection reagents were distilled off under reduced pressure, and 100 g of ethanol was added to the residue, stirred and dissolved completely, and a mixture of 6.1 g of phosphoric acid and 60 g of methyl tert-butyl ether was added dropwise, and stirred for 4 h. Filter and dry to obtain the phosphate of telamycin. Add 140 mL of dichloromethane to the phosphate, add aqueous potassium carbonate solution (8.93 g of potassium carbonate, 140 mL of water) while stirring, and separate layers after stirring for 30 min, add 140 mL of dic...

Embodiment 3

[0039] Put 20 g of epoxide (compound 2), 100 g of methanol and 30 g of n-propylamine into a 250 mL three-necked flask, start stirring, and after the dissolution is complete, heat the oil bath to an internal temperature of 30 °C, and react at 30 °C for 24 h. Add 40 g of methylethylamine solution into the reaction bottle, and react at 30 °C for 12 h, and the reaction is monitored by HPLC. After the reaction finishes, all solvents and excess deprotection reagents are distilled off under reduced pressure, and 100 g of methyl tert-butyl ether is added to the residue, stirred and dissolved completely, and 6.1 g of trifluoroacetic acid and 60 g of methyl tert-butyl ether are added dropwise. The mixture was stirred for 4 h, filtered, and dried to obtain the trifluoroacetic acid salt of telamycin. Add 140 mL of dichloromethane to the trifluoroacetic acid salt, add potassium carbonate aqueous solution (potassium carbonate 8.93 g, water 140 mL) under stirring, and separate layers after s...

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Abstract

The invention discloses a tulathromycin A synthesis method and belongs to the technical field of medicine synthesis. The tulathromycin A synthesis method comprises 1, dissolving a compound 2 into a solvent 1 and carrying out a reaction process on n-propylamine at a temperature of 20-80 DEG C, 2, after the reaction, according to reaction product benzyloxycarbonyl removal cases, directly carrying out a reaction process at a temperature of 20-80 DEG C, or adding a deprotection regent into the reaction product and then carrying out a reaction process on the mixture at a temperature of 20-80 DEG C, and separating the reaction products to obtain a tulathromycin A crude product, and 3, purifying the tulathromycin A crude product to obtain a tulathromycin A refined product. The tulathromycin A synthesis method realizes deepoxidation and deprotection by one process, shortens reaction time, improves reaction efficiency and reduces a cost.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a synthesis method of telamycin A. Background technique [0002] Tulathromycin is a macrolide semi-synthetic antibiotic specially used for animals. Tulathromycin is mainly used for the breathing of pigs and cattle caused by Actinobacillus, Mycoplasma, Pasteurella and Haemophilus para For systemic diseases, it has many advantages such as less dosage, one-time administration, low residue and animal-specific. At present, the method of Tyramycin A at home and abroad is mainly as follows: Dihydrohomoerythromycin (demethylazithromycin) is a raw material, through steps such as CbzCl protection, Swem oxidation, epoxidation, deprotection, amination reaction (EP1253153A1 ), the process route is as follows: [0003] [0004] The inventor finds when realizing above-mentioned technology: [0005] Dimethyl sulfide is generated in the synthetic reaction proces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/00
CPCC07H1/00C07H17/00
Inventor 彭要武田文敬丁思航岳荣耀
Owner MASTEAM BIO TECH
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