ChemicalBook CAS DataBase List Moxidectin

Moxidectin synthesis

5synthesis methods

Product Name:Moxidectin
CAS Number:113507-06-5
Molecular formula:C37 H53 N O8
Molecular Weight:639.82

Moxidectin is an anthelmintic drug which kills parasitic worms (helminths), and is used for the prevention and control of heartworm and intestinal worms. Moxidectin is a semisynthetic derivative of nemadectin which is produced by fermentation by Streptomyces cyano-griseus. This Streptomyces species was discovered in a soil sample from Australia in the late 1980s collected by an agronomist working for the American Cyanamid company. Synthetic Description Reference: Beddall, Nicola E.; Howes, Peter D.; Ramsay, Michael V. J.; Roberts, Stanley M.; Slawin, Alexandra M. Z.; Sutherland, Derek R.; Tiley, Edward P.; Williams, David J. Chemical transformations of S541 factors (A)-(D): preparation and reactions of the 23-ketones. Tetrahedron Letters. Volume 29. Issue 21. Pages 2595-8. Journal. (1988). Synthetic Description Reference: He, Yongwai; Wen, Jing; Zhang, Honglan. Method for preparing Moxidectin. Assignee Peking University Founder Group Co., Ltd., Peop. Rep. China; Chongqing Daxin Pharmaceutical Co., Ltd., PKU International Healthcare Group; PKU International Hospital Group Co., Ltd. CN 104277050. (2015). Synthetic Description Reference: Dai, Yao; Du, Zhibo; Wang, Rongliang. Preparation of Moxidectin. Assignee Dalian Jiuxin Biological Chemical Science and Technology Co., Ltd., Peop. Rep. China. CN 104017001. (2014). Synthetic Description Reference: Massara, Pasquale; Miraglia, Guiseppe; Caraco, Marco; Sapienza, Stefania; Patel, Jignesh. Improved oxidation process with enhanced safety and use thereof. Assignee Wyeth, John, and Brother Ltd., USA. AU 2006100660. (2006).

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

Reference: Beddall, Nicola E.; Howes, Peter D.; Ramsay, Michael V. J.; Roberts, Stanley M.; Slawin, Alexandra M. Z.; Sutherland, Derek R.; Tiley, Edward P.; Williams, David J. Chemical transformations of S541 factors (A)-(D): preparation and reactions of the 23-ketones. Tetrahedron Letters. Volume 29. Issue 21. Pages 2595-8. Journal. (1988).

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Yield:113507-06-5 88.6%

Reaction Conditions:

with N-methoxylamine hydrochloride;sodium acetate in methanol at -10 - 0; for 8 h;

Steps:

1.D; 8-9 D. Preparation of Moxectine (I)

Add 23-oxonimoxine (IV) (611g, 1.0mol), anhydrous sodium acetate (395g) and methanol (3600g) into the reactor, stir well and cool to -10 to 0, then stir again Add methoxyamine hydrochloride (183.7g, 2.2mol) in batches. During the addition, control the temperature of the mixture to not exceed 0°C. After the addition is complete, keep stirring and react under 0°C for 8 hours. After the reaction, add dropwise Adjust the pH value of the mixture to neutral with 5% sodium bicarbonate aqueous solution, and then add dichloromethane (6100g) to it for extraction. After separation, the organic phase is dried with anhydrous sodium sulfate. After drying, the desiccant is removed by filtration and the filtrate is concentrated. Obtained oil, recrystallized from methanol to obtain moxectine (I) fine product, 566.8g as a light yellow powder, the yield is about 88.6%,

References:

CN111592553,2020,A Location in patent:Paragraph 0046; 0053-0054; 0073-0078

593-56-6 Synthesis