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2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine synthesis method

A technology of cytosine nucleoside and synthesis method, which is applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of complex methods, high raw material prices, unfavorable industrial production, etc., and achieves the effect of simple methods

Active Publication Date: 2014-01-22
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The raw material price of above-mentioned method is higher, and method is more complicated, is unfavorable for carrying out suitability for industrialized production

Method used

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  • 2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine synthesis method
  • 2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine synthesis method
  • 2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine synthesis method

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0023] Example 1: Using dichloromethane as a solvent and pyridine as an organic base.

[0024] Take 20g of 2,3-di-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine nucleoside into a 500ml four-necked bottle, add 200ml of dichloromethane and 20ml of pyridine , start stirring, control the reaction temperature at 25°C, and slowly introduce CO 2 After 5 hours, add 150ml of purified water to wash for 30 minutes, static layering, after separating the organic layer, add 150ml of purified water and wash for 30 minutes, static layering, after separating the organic layer, concentrate the organic layer under reduced pressure, the temperature of the water bath is 40°C, concentrated to dryness under reduced pressure to obtain a white solid, and then added 60ml of isopropanol to recrystallize to obtain 10.9g of a white solid with a purity of 99.2% and a yield of 62.7%.

example 2

[0025] Example two: using dichloromethane as a solvent and triethylamine as an organic base.

[0026] Take 20g of 2,3-di-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine nucleoside into a 500ml four-necked bottle, add 200ml of dichloromethane, triethyl Amine 28ml, start stirring, control the reaction temperature 25°C, slowly feed CO 2 After 5 hours, add 150ml of purified water to wash for 30 minutes, static layering, after separating the organic layer, add 150ml of purified water and wash for 30 minutes, static layering, after separating the organic layer, concentrate the organic layer under reduced pressure, the temperature of the water bath is 40°C, concentrated to dryness under reduced pressure to obtain a white solid, and then added 60ml of isopropanol for recrystallization to obtain 9.1 g of an off-white solid with a purity of 97.8% and a yield of 52.6%.

example 3

[0027] Example three: using toluene as a solvent and pyridine as an organic base.

[0028] Take 20g of 2,3-di-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine nucleoside into a 500ml four-necked bottle, add 200ml of toluene and 20ml of pyridine, and open Stir, control the reaction temperature at 25°C, and slowly introduce CO 2 After 5 hours, add 150ml of purified water to wash for 30 minutes, static layering, after separating the organic layer, add 150ml of purified water and wash for 30 minutes, static layering, after separating the organic layer, concentrate the organic layer under reduced pressure, the temperature of the water bath is 40°C, concentrated to dryness under reduced pressure to obtain a white solid, and then added 60ml of isopropanol to recrystallize to obtain 10.2g of a white solid with a purity of 98.6% and a yield of 58.9%.

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Abstract

The invention discloses a 2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine synthesis method. According to the method, 2,3-di-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine is adopted as a raw material, and is dissolved by using an organic solvent; organic alkali is added; CO2 is delivered in; and a reaction is allowed under a reaction temperature controlled at 0-50 DEG C and a reaction time controlled at 1-24h. According to the method, an intermediate of a capecitabine production process is used for preparing capecitabine impurity C2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine. The raw materials are easier to obtain, and the method is more simplified.

Description

technical field [0001] The present invention relates to a synthesis method of capecitabine impurity C (2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine nucleoside) , belonging to the field of medical technology. Background technique [0002] Capecitabine (Capecitabine) is an anti-metabolite fluoropyrimidine deoxynucleoside carbamate drug that can be converted into 5-FU in the body. It is developed by Roche and its trade name is Xeloda. It can inhibit cell division and interfere with RNA and protein synthesis. With the widespread promotion of capecitabine, more and more people pay attention to the research on its impurities. [0003] Capecitabine impurity C, chemical name: 2',3'-O-carbonyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine, CAS number: 921769-65 -5, molecular formula: C 16 h 20 N 3 o 7 F, molecular weight: 385.3443. Its chemical structural formula is shown below. [0004] [0005] The synthetic method of the impurity C of existi...

Claims

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Application Information

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IPC IPC(8): C07H19/06C07H1/00
Inventor 赵孝杰吕红超王超
Owner SHANDONG BOYUAN PHARM CO LTD
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