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Synthesis method of capecitabine

A synthetic method, capecitabine technology, applied in the field of chemical drug synthesis, to achieve the effects of reduced production costs and simplified synthetic processes

Inactive Publication Date: 2013-07-10
JINING HIGH TECH DEV ZONE YONGFENG CHEM PLANT
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Problems solved by technology

[0005] In order to solve the problem of using 5-deoxy-triacetyl ribose and 5-fluorocytosine as raw materials in the above prior art, the intermediate 2',3'-di Acetoxy-5'-deoxy-5-fluorocytidine and capecitabine are synthesized from high cost and low conversion rate due to the presence of isomers of 5-deoxy-triacetyl ribose. The invention provides a synthetic method of capecitabine capable of simultaneously reacting 5-deoxy-triacetyl ribose α, β isomers and increasing the conversion rate

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  • Synthesis method of capecitabine

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[0027] In order to better understand the present invention, the following will be further described in conjunction with specific examples.

[0028] (1) Put toluene (206 g), HMDS (79.38 g), 5-fluorocytosine (59.58 g), and ammonium sulfate (2.4 g) into a 1000 ml reaction bottle, stir and heat up to reflux, dissolve in about 2 hours, and then reflux For 1 hour, recover the solvent under reduced pressure (about 80°C) to dryness, cool down to below 30°C, add dichloromethane (1010.26g), 5-deoxy-1,2,3-triacetoxy-D-ribose is α, β isomer mixture (120g), in which the molar ratio of α, β isomer is 2.7:1, cool down to 20°C, add trifluoromethanesulfonic acid (8.372ML) dropwise, control < 25°C, drop for about 2 hours After completion, heat preservation reaction at 25°C for 12 hours to obtain reaction solution a;

[0029] (2) Transfer the reaction solution a into a 2000ml reaction bottle, add sodium bicarbonate (232.64g), add water (400g) dropwise, and drop it for about 1-2 hours, stir for ...

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Abstract

The invention relates to the technical field of synthesis of chemical medicines, and in particular relates to a synthesis method of capecitabine. The synthesis method of the capecitabine comprises the following steps: reacting 5-flucytosine with 5-deoxy-1,2,3-triacetoxy-D-ribose in the presence of a catalyst; performing aftertreatment on the reaction liquid to obtain 2',3'-diacetoxy-5'-deoxy-5-fluorocytidine; adding pentyl chloroformate dropwise into the 2',3'-diacetoxy-5'-deoxy-5-fluorocytidine and pyridine; and performing aftertreatment on the reaction liquid, adding alkaline liquid dropwise and performing treatment to obtain the capecitabine, wherein the catalyst comprises trifluoromethanesulfonic acid and derivatives thereof. The catalyst used in the method can use alpha, beta isomer mixed type 5-deoxy-triacetyl ribose as a raw material and does not need to separate ALFA and BETA isomers; and the generated ALFA type glucoside can be converted into BETA type glucoside, so the production process is simplified and the production cost is reduced.

Description

[0001] technical field [0002] The invention relates to the technical field of chemical drug synthesis, in particular to a synthesis method of capecitabine. [0003] Background technique [0004] Capecitabine (Capecitabine), the chemical name is 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl] cytidine, capecitabine itself is not cytotoxic, and it is metabolized by enzymes in the body For 5-fluorouracil (5-FU), and then play an anti-tumor effect. The concentration of enzymes related to capecitabine metabolism in tumor tissue is higher than that in normal tissue, so that it has selective cytotoxicity to tumor cells and can be used as an oral cytotoxic agent. Its structural formula is as follows: [0005] [0006] There are many synthetic methods of capecitabine reported so far. Among them, 5-deoxy-triacetyl ribose and 5-fluorocytosine are used as raw materials to synthesize the intermediate 2',3'-diacetoxy-5'-deoxy -5-fluorocytidine, and then synthesize capecitabine, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/06C07H1/00
Inventor 王敦海周在国
Owner JINING HIGH TECH DEV ZONE YONGFENG CHEM PLANT
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