New method for preparing peramivir key intermediate

A technology of intermediates and new methods, applied in the field of drug synthesis, can solve problems such as difficult mass production, complicated process, and low yield

Active Publication Date: 2012-10-31
PHARMA SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, reduction ring-opening and acetylation are completed in two steps, and a relatively tedious post-treatment process is required in the middle. The acetylation is carried out after separation and purification of the product after reduction ring-opening. The process is complex and the yield is low, which is not easy for mass production.

Method used

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  • New method for preparing peramivir key intermediate
  • New method for preparing peramivir key intermediate
  • New method for preparing peramivir key intermediate

Examples

Experimental program
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Embodiment 1

[0022] (1S, 2S, 3S, 4R, 1'S)-3-(1-acetylamino-2-ethylbutyl)-4-(Boc)-amino-2-hydroxycyclopentane-1-carboxylic acid methyl ester ( I) preparation:

[0023]

[0024] Compound II (1g, 2.82mmol), NiCl 2 ·6H 2 O (0.7g, 2.94mmol) was dissolved in a mixed solvent of 10mL methanol and 5mL tetrahydrofuran, cooled to -15°C, and NaBH 4 (0.3g, 7.9mmol) was slowly added to the above system, and the reaction was stirred after the addition (maintain the system temperature -5--10°C), and monitored by TLC (PE:EtOAC=5:1, color development in iodine cylinder). After the raw materials disappeared, acetic anhydride (3 g, 26 mol) was added dropwise to the reaction system, and stirring was continued at 0° C. for 2 hours (TLC:DCM:MeOH=10:1, the solution changed from black to green). Adjust the pH value to 9.6 with 25% ammonia water (2.6g, 0.038mol), spin off the methanol at low temperature, then add 20mL of water and 30mL of ethyl acetate to stir and separate the layers, and back-extract the aqu...

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Abstract

The invention discloses a method for preparing a peramivir key intermediate. According to the method for preparing the peramivir key intermediate, an intermediate (II) is taken as a raw material; and after reductive ring opening, post-processing of a reaction system is not required, and an acetylating agent is added by a one-pot method so as to obtain a peramivir intermediate (I) (1S, 2S, 3S, 4R, 1'S)-3-(1-acetamido-2-ethylbutyl)-4-(Boc)-amino-2-hydroxy-cyclopentane-1-carboxylate. Through the adoption of the method, a middle complicated post-processing process is omitted and the acetylating agent is directly used for quenching and acetylating, so that the method is simple in operation and the yield is greater than 80%.

Description

technical field [0001] The invention relates to a key intermediate for preparing peramivir (1S, 2S, 3S, 4R, 1'S)-3-(1-acetylamino-2-ethylbutyl)-4-(Boc)-amino-2 The invention relates to a new method of -hydroxycyclopentane-1-carboxylate, which belongs to the field of drug synthesis. Background technique [0002] Peramivir, English name Peramivir, chemical name (1S, 2S, 3S, 4R, 1'S)-(-)-3-[(1'-acetylamino-2'-ethyl)butyl]-4{ [(aminoimino) methyl] amino} 2-hydroxycyclopentane-1-carboxylic acid, the structural formula is as shown in I. The drug is a cyclopentane derivative neuraminidase inhibitor developed by American Biocrystal Pharmaceutical Co., Ltd., which can effectively inhibit the replication of various influenza viruses, has good tolerance, low toxicity, and can Injection and other advantages, is a promising anti-influenza virus drugs. [0003] [0004] Patent documents related to the synthesis method of peramivir in the prior art include CN1227466, CN1367776, CN1282...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/24C07C269/06
Inventor 彭少平蒋胜力蔡振伟安荣昌王伟华董学军
Owner PHARMA SHANGHAI
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