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Preparation method of cationic liposome SM-102 and analogue thereof
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A technology of cationic liposomes and analogs, applied in the preparation of organic compounds, cyanide reaction preparation, carboxylate preparation, etc., can solve the problems of long time, difficult to control, and large pollution
Pending Publication Date: 2022-08-09
湖北英纳氏生物科技有限公司
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It solves the problems of difficult control, long time, poor selectivity, cumbersome operation, low yield and large pollution in traditional synthetic reactions
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Embodiment 1
[0045] Example 1 Preparation of methyl 8-bromooctanoate (intermediate 1)
[0046] Add 600g of 8-bromooctanoic acid into a 3000mL reaction flask, add 2000ml of methanol, add 10g of concentrated sulfuric acid, heat at 50-65°C until the reaction is complete, cool to room temperature, add sodiumcarbonate to adjust to alkalinity, filter to remove insoluble solids, and recover methanol to obtain 8 -Methyl bromooctanoate 605g, yield 95%.
Embodiment 2
[0047] Example 2 Preparation of 8-bromooctanoic acid-9-heptadecanol ester (intermediate 2)
[0048] 600g of methyl 8-bromooctanoate was added into the 5000mL reaction flask, 650g of 9-heptadecanol was added, 2000ml of n-heptane as solvent, 10g of glycidol as a catalyst, heated to 80-90°C and stirred for 8h, and recovered after the reaction was completed. n-heptane to obtain 1165 g of colorless transparent liquid with a yield of 96%.
[0050] Example 3 Preparation of 6-bromohexanoic acid-undecyl ester (intermediate 3)
[0051] Add 1000g of 6-bromohexanoic acid, 885g of undecyl alcohol to the 3000L reaction flask, add 30g of catalyst potassiumhydrogensulfate, depressurize the water pump to the reaction pressure of 10-20mmHg, and heat to the inner temperature of 80-85°C at the same time, it can be seen that there is water evaporated, After about 5-6 hours of reaction, basically no water was evaporated, the reaction flask had a constant weight, cooled to room temperature, and about 100 g of silica gel was placed in a Buchner funnel, and the reaction solution was filtered to obtain 1718 g of a light yellow transparent liquid with a yield of 96%.
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Abstract
The invention discloses a preparation method of cationic liposome SM-102 and analogues thereof, and belongs to the technical field of organic synthesis. According to the invention, a key intermediate secondary alcohol ester 8-bromocaprylic acid-9-heptadecanol ester is synthesized creatively by adopting a transesterification method, and 6-bromohexanoic acid-undecanol ester and 8-bromocaprylic acid-nonanol ester are synthesized by adopting a solvent-free decompression dehydration method. 6-ethanolamine-hexanoic acid-undecanol ester and 8-ethanolamine-octanoic acid-nonyl alcohol ester are synthesized by an alkanesolvent or aromatic hydrocarbonsolvent direct extraction method, and SM-102 and Lipid 5 are synthesized, purified and separated by a specific organic acid salifying crystallization method. The problems of difficulty in control, long time, poor selectivity, complexity and difficulty in operation, low yield and serious pollution in the traditional synthesis reaction are solved.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a cationic liposome SM-102 and an analog thereof. Background technique [0002] Liposomes were first discovered under the microscope in 1961 by scientists Alec Douglas. Bangham and R. W. Horne. Liposomes are vesicle structures composed of lipid molecules, and their lipid bilayers form a hydrophobic shell and an inner aqueous cavity, with both hydrophilic and hydrophobic properties. [0003] This property makes liposomes ideal vehicles for drug delivery. In 1995, the US FDA approved the first liposomal drug Doxil. Doxil uses HSPC / DMG-PEG two-component liposome-encapsulated drugdoxorubicin for ovarian cancer and breast cancerchemotherapy to reduce the toxicity of free drugs to other organs. [0004] In the formulation of lipid nanoparticles encapsulating nucleic acid, ionizable lipids or cationic liposomes play a key role, and their pKa values...
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