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Synthetic method of D-(+)-2-chloro-propanoyl chloride

The technology of a chloropropionyl chloride and a synthesis method, which is applied in the synthesis field of D--2-chloropropionyl chloride, can solve problems such as low product yield, and achieve high product yield, novel reaction catalyst and no environmental impact. Effect

Inactive Publication Date: 2008-10-15
HEBEI HUACHEN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention is used to solve the problem of low product yield in the synthesis method of existing D-2-chloropropionyl chloride, and provides a D-2-chloropropionyl chloride with simple process, high yield, cheap raw and auxiliary materials, environmental protection, and suitable for industrial production. -(+)-2-chloropropionyl chloride synthetic method

Method used

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  • Synthetic method of D-(+)-2-chloro-propanoyl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Step a, synthetic D-(+)-2-chloropropionic acid ethyl ester

[0019] A four-necked reaction flask equipped with mechanical stirring and a hydrogen chloride absorber was installed, 125 grams of thionyl chloride and 10 grams of calcium fluoride catalyst were added, and 100 grams of L-ethyl lactate was added dropwise at room temperature (actually 27° C.). After dripping, heat up to 65-70°C, stir at constant temperature for 2 hours, heat up to 168°C for reflux reaction for 15 hours, stop the reaction, cool the reaction solution to room temperature (actually 27°C), enter the rectification tank for rectification to obtain D -(+)-2-Ethyl chloropropionate, the yield is 89.6%, the purity of the product reaches 99.5%, the optical purity of the chiral GC analysis reaches 97.1%, and the optical rotation of the product is +19.2 degrees.

[0020] Step b, synthesis of D-(+)-2-chloropropionic acid

[0021] Set a four-necked reaction flask equipped with mechanical stirring, add 70 grams...

Embodiment 2

[0025] Step a, synthetic D-(+)-2-chloropropionic acid ethyl ester

[0026] Set up a reaction kettle equipped with mechanical stirring and a hydrogen chloride absorber, add 240 kg of thionyl chloride and 10 kg of calcium fluoride catalyst, start stirring, and at room temperature (actually 25°C), feed at a rate of 5 kg / min , add 200 kg of L-ethyl lactate, after adding L-ethyl lactate, heat up to 65-70°C and stir for 3 hours, then heat up to 170°C for reflux reaction for 15 hours, stop the reaction, cool to room temperature (actually 25 ℃), enter the rectifying kettle and carry out rectification to obtain the D-(+)-2-chloropropionic acid ethyl ester product, the productive rate is 79.7%, the purity of the product reaches 99.5%, and the chiral GC analysis optical purity reaches 97.1%, The optical rotation of the product is +19.2 degrees.

[0027] Step b, synthesis of D-(+)-2-chloropropionic acid

[0028] Set up the reactor that mechanical stirring is housed, add 140 kilograms of...

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Abstract

The invention relates to a method for synthesizing D-(+)-2-chloro-Propanoyl chloride, which is used for solving the problems that the product recovery rate of the prior synthetic method is low and the synthetic method is not suitable for industrial production. The method adopts the technical proposal that L-ethyl lactate and thionyl chloride react under the action of calcium fluoride catalyst to generate D-(+)-2-chloropropionic acid ethyl ester, D-(+)-2-chloropropionic acid ethyl ester is hydrolyzed under the action of caustic soda dissolving to generate D-(+)-2-chloropropionic acid, and D-(+)-2-chloropropionic acid reacts with the thionyl chloride to generate D-(+)-2-chloro-Propanoyl chloride. The method has the advantages that the method is novel, the process is simple, the product recovery rate is high, the cost of the catalyst is low, the catalyst is easy to obtain, the environment can not be affected, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of D-(+)-2-chloropropionyl chloride (ie D-2-chloropropionyl chloride). Background technique [0002] D-(+)-2-Chloropropionyl chloride is an important intermediate for the synthesis of N(2)-L-alanyl-L-glutamine (Lipeptide) The main intermediate and the starting material of drugs such as cloxoprofen sodium. Because L-glutamine is the amino acid with the most content in human blood, it has important physiological functions, but because of the low solubility and poor thermal stability of L-glutamine, it is easily decomposed into pyroglutamic acid and ammonia in aqueous solution. Harmful to the human body, thus limiting the clinical application of L-glutamine. And N(2)-L-alanyl-L-glutamine has high solubility in aqueous solution, can withstand high temperature sterilization, has good stability, and can be rapidly decomposed into L-glutamine and L-propanol in the human body. Amino acid makes up for the deficienc...

Claims

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Application Information

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IPC IPC(8): C07C53/50C07C51/60
Inventor 王有名马云段玉新吴忠华
Owner HEBEI HUACHEN PHARMA
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