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Preparation method of emtricitabine

A technology of emtricitabine and solvent, applied in the field of preparation of emtricitabine, can solve the problems of high synthesis cost of emtricitabine, difficult removal of chiral substrate, complicated process, etc. The effect of reduced synthesis cost and simple synthesis process

Active Publication Date: 2019-11-12
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

[0005] In view of this, the present invention aims to propose a method for preparing emtricitabine, to solve the problems of high synthetic cost, low yield, complex process and difficult removal of chiral substrates in existing emtricitabine

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Embodiment 1

[0028] A preparation method for emtricitabine, specifically comprising the following steps:

[0029] 1) Preparation of mandelic acid ester compounds: add 15.2g (0.1mol) (S)-(+)-mandelic acid, 12.9ml (0.16mol) pyridine and 150ml dichloromethane solution in the reactor, cool to -5 ℃, stir evenly; dissolve 13.9ml (0.12mol) of benzoyl chloride in 40ml of dichloromethane, slowly and uniformly drop it into the reactor, keep it warm for 1h, then raise the temperature to 25°C, react for 3h, make (S)- The hydroxyl protection reaction of (+)-mandelic acid and benzoyl chloride is fully carried out. After the reaction is stopped, the reaction solution is washed twice with saturated sodium bicarbonate, once with saturated brine, and then washed with anhydrous MgSO 4 Dried, suspended and evaporated to remove the solvent to obtain 24.0g of solid mandelic acid ester compounds, after calculation, its yield was 83.78%;

[0030] 2) Preparation of mandelic acid diester compound: add 12.8g (0.05m...

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Abstract

The invention provides a preparation method of emtricitabine. The preparation method comprises the steps: condensing (S)-(+)-mandelic acid serving as a chiral auxiliary with haloacetaldehyde glycol, carrying out hydrolysis, then, condensing a hydrolyzed product with 2,5-dihydroxy-1,4-dithiane to generate 5-hydroxy-1,3-oxythioheterocyclopentane-2-methyl ester, halogenating the intermediate, then, coupling the halogenated product to silanized 5-flucytosine, and finally, carrying out hydrolysis to prepare emtricitabine. The raw materials used in the whole synthesis process are cheap and available, so that the synthesis cost of emtricitabine provided by the invention is greatly reduced; moreover, the synthesis process is simple, the synthesis condition is mild, and the yield of the obtained emtricitabine is relatively high; and meanwhile, a chiral substrate is easy to remove in a synthesis process, few wastewater, waste gas and waste residue pollutants are generated, and the preparation method is suitable for large-scale industrial production of emtricitabine.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of emtricitabine. Background technique [0002] Nucleoside analogs and their derivatives are important nucleoside reverse transcriptase inhibitors, which have good antiviral activity against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). Tritabine and lamivudine. Emtricitabine (FTC) was developed by Gilead Science of the United States and was first launched in the United States in July 2003. Its chemical name is: (2R,5S)-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-2(1F)-pyrimidine Ketones, whose chemical structure is shown below: [0003] [0004] At present, there are many preparation methods for emtricitabine, but there are following problems in the existing emtricitabine synthesis process: the synthesis process is complex, the reaction conditions are harsh, the requirements for process equipment are high, the sele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D411/04
CPCC07D411/04Y02P20/55
Inventor 刘生鹏顾继山吴晓宇许莉莉熊芸孙国锋丁一刚
Owner WUHAN INSTITUTE OF TECHNOLOGY
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