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Method for preparing Zidovudine azide intermediate by phase transition method

A zidovudine and phase transfer technology, applied in sugar derivatives, organic chemistry, etc., can solve the problems of easy explosion of azide reagents and long reaction time, and achieve the advantages of reducing hidden dangers in production, short reaction time and mild operating conditions. Effect

Active Publication Date: 2008-06-04
SHANGHAI DESANO CHEM PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method for upper azide introduced in the literature is all carried out at a temperature higher than 100°C, and the reaction time is long (seeing US5124442 and Synthesis, 1991 (3), 39-40), and the azide reagent used has an explosive characteristic

Method used

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  • Method for preparing Zidovudine azide intermediate by phase transition method
  • Method for preparing Zidovudine azide intermediate by phase transition method

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Under the protection of argon, dissolve 5g of zidovudine oxygen bridge in 100ml of DMF, then add 4.2g of sodium azide, 7g of tetrabutylammonium bromide, and 0.6g of ammonium chloride in sequence, stir evenly, and heat up Reflux at 80°C for 6 hours. After the reaction was completed, it was cooled to room temperature, filtered, and the filtrate was concentrated to dryness under reduced pressure. Add 100ml of dichloromethane and 50ml of water to the residue to dilute, separate the organic layer, back-extract the aqueous layer with 20ml×2 of dichloromethane, combine the organic layers, wash with 50ml×3 of water, and dry over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to dryness under reduced pressure, and dried in vacuum with phosphorus pentoxide to obtain 0.95 g of zidovudine azide intermediate, with a yield of 87%.

Embodiment 2

[0023] Under the protection of argon, dissolve 5g of Zidovudine bridge oxide in 100ml of DMF, then add 4.2g of sodium azide, 7g of tetrabutylammonium bromide, and 1.4g of ammonium sulfate in sequence, stir well, and heat up to 80 °C reflux for 6.5 hours. The reaction treatment was the same as in Example 1 to obtain 1.0 g of the product, with a yield of 91%.

Embodiment 3

[0025] Under the protection of argon, dissolve 5g of Zidovudine bridge oxide in 100ml of DMF, then add 4.2g of sodium azide, 7g of tetrabutylammonium bromide, 5.0g of 001*7 strong acid resin, and stir well , heated to 80°C and refluxed for 6 hours. The reaction treatment was the same as that in Example 1 to obtain 0.90 g of the product, with a yield of 82%.

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Abstract

The invention discloses a method which adopts a phase transfer method to prepare Zidovudine azide intermediate, comprising the following steps: Zidovudine oxy-bridged compound reacts with sodium azide in the solution, in which a phase transfer catalyst and a phase transfer ancillary reagent exist, and then the Zidovudine azide intermediate is collected from the reaction product. The method of the invention has moderate operational conditions, short reaction time and a reaction yield of 91 percent, thereby increasing production hidden dangers greatly.

Description

technical field [0001] The invention relates to a method for preparing a zidovudine azide intermediate, in particular to a method for preparing a zidovudine azide intermediate by a phase transfer method. Background technique [0002] Zidovudine is the first FDA-approved anti-AIDS (AIDS) drug, and its azide intermediate (I) is a key intermediate in its synthetic route. The method for upper azide introduced in the literature is all carried out at a temperature higher than 100°C, and the reaction time is long (seeing US5124442 and Synthesis, 1991 (3), 39-40), and the azide reagent used has an explosive characteristic. [0003] [0004] In the formula, R is selected from alkyl, hydroxyalkyl or acyl. Contents of the invention [0005] The technical problem to be solved by the present invention is to provide a method for preparing a zidovudine azide intermediate by a phase transfer method, so as to overcome the above-mentioned defects in the prior art. [0006] Method of t...

Claims

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Application Information

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IPC IPC(8): C07H19/073
Inventor 李金亮周夏君
Owner SHANGHAI DESANO CHEM PHARMA
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