Preparation method for nucleoside compounds

A technology for nucleoside compounds and compounds, which is applied in the production of organic chemistry and bulk chemicals to achieve the effect of easy availability of raw materials and high product yield

Inactive Publication Date: 2008-03-26
严红芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

When using domestic raw materials to produce the above products, the yield is only 50% of the disclosed yield, therefore, it is necessary to provide a new preparation method to reduce production costs and increase yield

Method used

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  • Preparation method for nucleoside compounds
  • Preparation method for nucleoside compounds
  • Preparation method for nucleoside compounds

Examples

Experimental program
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Embodiment Construction

[0020] 1. [1s-(1α, 2β, 3α, 5β)]-5-succinimide-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentanol (formula 3 compound) preparation:

[0021] In a 2L three-neck flask, add 600ml of anhydrous DMF and 65g (0.66mol) of succinimide, add 2.3g of LiH (0.33mol) while stirring, continue stirring for 30min, and the solution becomes clear. Add 102.3g (0.33mol) of the compound of formula 3 dropwise, heat up to 120°C, and react for 3h. TLC showed that the reaction of the raw materials was complete, cooled to room temperature, and added 22ml of glacial acetic acid. Continue to stir for 10 minutes, add 1000ml of water and 400ml of ethyl acetate, stir, and separate layers. The aqueous phase was extracted once with ethyl acetate and the organic phases were combined. Dry over anhydrous magnesium sulfate. Evaporate to dryness under reduced pressure and separate on a silica gel column to obtain 90 g of pure compound of formula 3.

[0022] 2. [2R-(2α, 3β, 5α)]-5-succinimide-3-(benzyloxy)-2-[(ben...

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Abstract

The present invention relates to nucleoside compound preparing process, and is especially preparation process of 2-amino-9-[(1S, 3S, 4S)-4-hydroxy-3-hydroxymethyl-2-methyleneamyl]-1, 9-dihydro-6-H-purine-6-one. The initial materials [1s-(1alpha, 2beta, 3alpha, 5alpha)]-3-(benzylozy)-2-[( benzylozy) methyl]-6-oxa cyclic compound [3.1.0] and hexane are aminated, dess-mardin oxidized and nysted methylenated to obtain one intermediate compound; the intermediate compound is condensated with 2-amino-4-chloro-5-nitropyrimidinyl one as one other antiviral intermediate; and the condensation product is finally reacted through cyclization, hydrolysis, etc to obtain the target compound. The present invention has facile material and high product yield.

Description

Technical field [0001] A preparation method of a nucleoside compound of the present invention, specifically relates to 2-amino-9-[(1S,3S,4S)-4-hydroxyl-3-hydroxymethyl-2-methylenepentyl]-1,9- The preparation method of dihydro-6-H-purin-6-one [0002] Formula 1. Background technique [0003] The compound of formula 1 is a drug for treating hepatitis B virus developed by Bristol-Myers Squibb Company of the United States. It was approved for marketing in China in November 2005. It is one of the drugs for treating hepatitis B virus at present, and the market price is 39 yuan / tablet. Bristol-Myers Squibb has successively applied for raw material preparation methods in China, the patent application numbers are: 91110831.9, 200380105614, and preparations and other patents. When using domestic raw materials to produce the above products, the yield is only 50% of the disclosed yield. Therefore, it is necessary to provide a new preparation method to reduce production costs and inc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/18
CPCY02P20/55
Inventor 严红芳
Owner 严红芳
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