Synthesis method of acetaldehyde alcohol optical active ester

A technology of optical activity and synthesis method, which is applied in the field of drug synthesis, can solve the problems of low product yield, complex synthesis process, and low atom utilization rate, and achieve good reaction selectivity, simple synthesis process, and cheap and easy-to-obtain starting materials Effect

Pending Publication Date: 2021-05-07
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

[0005] In view of this, the present invention aims to propose a synthetic method of acetaldehyde optically active ester, to solve the existing problems of complex synthetic process of acetaldehyde optically active ester, low atom utilization rate and low product yield

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  • Synthesis method of acetaldehyde alcohol optical active ester
  • Synthesis method of acetaldehyde alcohol optical active ester

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Embodiment 1

[0025] A kind of synthetic method of acetaldehyde optically active ester, specifically comprises the following steps:

[0026] 1) Preparation of L-menthyl chloroformate: Add 20ml of dichloromethane into the reactor, place the instrument in a cold well, set the temperature to -10°C, and turn on the stirring paddle, then add 3.12g (0.02mol) of L-menth Alcohol, 2.376g (0.008mol) triphosgene, stir until completely dissolved, take the dropping funnel, add 1.896g (0.024mol) of pyridine and 40ml of dichloromethane and mix evenly, and slowly drop the solution into the reactor , the dropping rate is controlled at 1 drop per second, and the reaction is stirred for 4 hours to obtain a liquid phase containing L-menthyl chloroformate, and the second step of the reaction is ready to start after the reaction is determined to be complete by TLC detection;

[0027] 2) Preparation of bismenthyl carbonate: add the liquid phase containing L-menthyl chloroformate in the first step into the reactor...

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Abstract

The invention provides a synthesis method of an acetaldehyde alcohol optical active ester, which comprises the following steps of: reacting L-menthol as a raw material with triphosgene to obtain L-menthyl chloroformate, reacting the L-menthyl chloroformate with 1, 4-cis-butenediol, recrystallizing, and carrying out oxidation reaction under an ozone condition to obtain the acetaldehyde alcohol optical active ester. In the whole synthesis process, the initial raw materials are low in price and easy to obtain, the synthesis process is simple, the synthesis conditions are mild, and the synthesis cost of the acetaldehyde alcohol optical active ester is greatly reduced. The raw materials are good in reaction selectivity and high in atom utilization rate, and the obtained acetaldehyde alcohol optical active ester has high yield and purity. Meanwhile, few three-waste pollutants are generated in the synthesis process, and the method is suitable for industrial large-scale production of the acetaldehyde alcohol optical active ester, so that large-scale synthesis of drugs such as emtricitabine and lamivudine is facilitated.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing acetaldehyde optically active esters. Background technique [0002] Acetaldehyde optically active ester is an active intermediate for the preparation of drugs such as emtricitabine and lamivudine. The clinical test results of these two drugs show that they can both have significant virus inhibitory effects on HIV and hepatitis B HBV. The preparation of the intermediate acetaldehyde optically active ester plays a decisive role in the entire drug synthesis process, and its chemical structure is as follows: [0003] [0004] The Chinese invention patent with the notification number CN101125872A discloses a method for synthesizing acetaldehyde optically active esters. This method uses L-menthol and triphosgene to react to obtain L-menthyl chloroformate, and then condenses with acetone glycerol under acidic conditions. Open the ring, and finally ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C68/06C07C69/96
CPCC07C68/00C07C68/06C07C2601/14C07C69/96
Inventor 刘生鹏张宇顾继山吴晓宇许莉莉熊芸孙国锋丁一刚
Owner WUHAN INSTITUTE OF TECHNOLOGY
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