162204-20-8Relevant articles and documents
Multinuclear NMR measurements and DFT calculations for capecitabine tautomeric form assignment in a solution
Cmoch, Piotr,Krzeczyński, Piotr,Le?, Andrzej
, (2018)
The molecular structure of capecitabine (a widely applied prodrug of 5-fluorouracil) was studied by multinuclear NMR measurements and DFT quantum mechanical calculations. One or two tautomeric forms in a solution were detected depending on the solvent used. In the organic solvents, a mixture of two forms of capecitabine was observed: carbamate and imine tautomers. In the aqueous solution, only the carbamate form was found. The methylation of capecitabine yields mainly two products in different proportions: N3-methylcapecitabine and N7-methylcapecitabine. The protonation of capecitabine in organic solvents with perchloric acid occurs at the N3 nitrogen atom. DFT calculations strongly support the results coming from the analysis of the NMR spectra.
Cytidine derivative and method for preparing capecitabine medicines through derivative
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Paragraph 0074-0077, (2020/05/14)
The invention discloses a 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as shown in a general formula (I) and a preparation method of the derivative, and a method for preparing a N4-deoxycarbonyl cytidine derivative and antitumor medicines namely capecitabine by using the general formula (I) as a raw material, wherein the structure of the general formula (I) is as shown in the description. The 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as the raw material of a reaction is used as a glycosyl donor and can be activated under the condition of Lewis acid trimethylsilyl trifluoromethanesulfonate and N-lodosuccinimide in catalysis quantity, so that Lewis acid in traditional use equivalent or excessive quantity is avoided, and a reaction system is mild, free from occurrence of other side reactions and efficient.
Synthesis method of capecitabine intermediate
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Paragraph 0024-0026, (2018/06/15)
The invention provides a synthesis method of a capecitabine intermediate. The synthesis method comprises the following steps of performing a reaction on 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine, carbonyldiimidazole and n-pentanol at a low temperature to produce 2', 3'-di-O-acetyl-5'-deoxy-5-fluoro-N4-(n-pentyloxycarbonyl) cytidine. By the synthesis method, the reaction yield is increased, and the yield is higher than or equal to 91%. By the synthesis method, the step is simple, the operation is convenient, few byproducts are produced, and industrial production is facilitated.