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New method for preparing cytidine

A new method, the technology of cytidine, which is applied in the field of nucleoside preparation, can solve the problems that the preparation method of cytidine has not been reported in the literature, and achieve the effects of favorable production yield, good stability and stable reaction

Inactive Publication Date: 2012-08-15
江苏笃诚医药科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the method for preparing cytidine of the present invention has not been reported in the literature

Method used

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  • New method for preparing cytidine
  • New method for preparing cytidine
  • New method for preparing cytidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Acidic or partially acidic ionic liquid (Ionic Liquid, abbreviated as: IL) catalysts prepared a batch of combinations according to the following table 1 (the preparation method is referred to: Deng Youquan, Ionic Liquid---Properties, Preparation and Application, Beijing: China Petrochemical Press, 2006, p11-18) as a representative.

[0029] Table 1 Acidic or partially acidic ionic liquid catalysts

[0030]

[0031] Note: R in the table is n-butyl.

Embodiment 2

[0033] Preparation of cytidine

[0034]

[0035] 1.38g (4.33mmol) N 4 , O 2 -Dibenzoylcytosine and 1.53g (4.80mmol) tetraacetylribose were dissolved in 15mL of 1,2-dichloroethane, and the catalyst --- acidic ionic liquid 1a about 108mg (0.48mmol) was added at room temperature, and stirred 15h, thin plate chromatography detection, the reaction is complete. Add 20mL of ice water to the reaction solution, stir and separate the organic phase, then extract the water phase twice with 1,2-dichloroethane, combine the organic phases, dry over anhydrous sodium sulfate, concentrate and recover the solvent under negative pressure , to obtain a viscous intermediate. Then add 10 mL of 25% NH 3 - Methanol solution, react at 50-60°C for 4-5h, concentrate to dryness under negative pressure, add 5-7mL of methanol to dissolve the residue, and put the mixture in the refrigerator overnight. The resulting white solid precipitate was filtered, washed twice with a small amount of ice methanol...

Embodiment 3

[0039] Using the above raw material ratio and reaction conditions, and the operation method, the ionic liquid catalyst is changed, and the resulting cytidine yield is shown in the following table 2:

[0040] Cytidine productivity under different acidic ionic liquid catalyst conditions in table 2

[0041]

[0042] Note: "-" means not done.

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Abstract

The invention discloses a new method for preparing cytidine. The method adopts the acyl-protected carbohydrate and acyl-protected cytosine as reactants and the acid or meta-acid ionic liquid as a catalyst, and comprises the following steps of: reacting at a temperature of (-5)-55 DEG C in a solvent for 5-20 hours to obtain a corresponding acyl-protected cytidine derivative; and saponifying to remove the protecting group to obtain cytidine. The new method disclosed by the invention has the advantages that: the catalyst has a wide source and is easily available; and the reaction conditions are mild, the operation is convenient, the yield is relatively high, the pollution is little, and the method can be applied to large-scale production.

Description

technical field [0001] The invention belongs to the technical field of nucleoside preparation, and relates to a new method for preparing cytidine using an acidic or slightly acidic quaternary ammonium salt-type ionic liquid as a catalyst, that is, using acyl-protected sugars and acyl-protected cytosine as reactants, The ionic liquid is used as a catalyst to prepare cytidine, and the method of the invention is suitable for laboratory preparation and large-scale industrial production of cytidine. Background technique [0002] Cytidine and cytidine derivatives are not only one of the important raw materials for synthesizing nucleotides, but also important intermediates for synthesizing drugs. Many types of drugs contain structural units of cytidine and its analogs, and their demand is increasing day by day. Biochemical methods such as biological fermentation or separation of cytidine and cytidine derivatives from natural products have been unable to meet the market demand. Alth...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H19/06C07H19/067
CPCY02P20/55
Inventor 姚其正王笃政王玉祥姚世宁李民权
Owner 江苏笃诚医药科技股份有限公司
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