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Synthesis method of high-purity D-2-chloropropionyl chloride

A technology of D-2-, chloropropionyl chloride, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve the problem of unsuitable chemical plant economic cycle use, the purity of D-2-chloropropionyl chloride The problem is not high, the products and by-products are not easy to separate, etc., to achieve the effect of low equipment requirements, high reaction yield and purity, and easy handling

Active Publication Date: 2013-11-27
SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the known technology, the existing synthetic method of D-2 chloropropionyl chloride is to use food-grade L-lactic acid and thionyl chloride to obtain D-2 chloropropionyl chloride in a pot under the action of a catalyst, and this method produces a large amount of by-products , the products and by-products are not easy to separate, and a large amount of high polymer produced cannot be recycled, so it is not suitable for the economical recycling of chemical plants, and the final D-2-chloropropionyl chloride is not high in purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Step a, synthetic D-2-methyl chloropropionate

[0021] Add 110g of L-lactate methyl ester and 1.5g of pyridine to the dry reaction flask with stirring and condensation, cool down to -7°C in an ice-salt bath, add 140g of thionyl chloride dropwise, control the system temperature below 0°C, and add dropwise for 2 hours After completion, the ice-salt bath was pulled down and vacuum stirred for 1 hour, then the temperature was raised to 80°C, and refluxed for 4 hours. After the reaction solution dropped to 35°C, the SOCl gas was removed under reduced pressure. 2 , SO 2 Wait for the gas, after the gas is basically pumped out, add 30g of tap water and wash for 10min to obtain 128g of methyl chloropropionate with a yield of 99.2% and a purity of 99.6%.

[0022] Step b, synthesis of D-2-chloropropionic acid

[0023] Add 120g of methyl chloropropionate to the reaction flask with stirring, add 228g of 20% sodium hydroxide solution dropwise at a temperature below 10°C, finish add...

Embodiment 2

[0027] Step a, synthetic D-2-methyl chloropropionate

[0028] Add 150g of L-lactate methyl ester and 1.5g of pyridine to the dry reaction flask with stirring and condensation, cool down to -2°C in an ice-salt bath, add 190g of thionyl chloride dropwise, control the system temperature below 0°C, and add dropwise for 3 hours After completion, the ice-salt bath was pulled down and vacuum stirred for 2 hours, and then the temperature was raised to 60°C, and refluxed for 5 hours. After the reaction solution dropped to 35°C, the gases such as SOCl2 and SO2 were removed under reduced pressure. 174.6 g of methyl chloropropionate was obtained, with a yield of 99.2% and a purity of 99.4%.

[0029] Step b, synthesis of D-2-chloropropionic acid

[0030] Add 135g of methyl chloropropionate to a reaction flask with stirring, add 400g of 20% sodium hydroxide solution dropwise at a temperature below 5°C, and finish adding dropwise in 2 hours, keep warm at a temperature below 5°C for 3 hours,...

Embodiment 3

[0034] Step a, synthetic D-2-methyl chloropropionate

[0035] Add 150g of L-lactate methyl ester and 1.5g of pyridine to the dry reaction flask with stirring and condensation, cool down to -10°C in an ice-salt bath, add 190g of thionyl chloride dropwise, control the system temperature below 0°C, and add dropwise for 3 hours After completion, the ice-salt bath was pulled down and vacuum stirred for 2 hours, and then the temperature was raised to 55°C, and refluxed for 5 hours. After the reaction solution dropped to 35°C, the gases such as SOCl2 and SO2 were removed under reduced pressure. 174.6 g of methyl chloropropionate was obtained, with a yield of 99.2% and a purity of 99.4%.

[0036] Step b, synthetic D-2-chloropropionic acid

[0037] Add 135g of methyl chloropropionate to the reaction flask with stirring, add 270g of sodium hydroxide solution with a mass fraction of 20% below 5°C dropwise, after 2 hours to complete the dropwise addition, keep warm at below 5°C for 3 hou...

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PUM

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Abstract

The invention provides a synthesis method of high-purity D-2-chloropropionyl chloride. A process path of chlorination, hydrolysis and chloroacylation of L-methyl lactate is adopted. Specifically, the synthesis method sequentially comprises the following steps: (1) the synthesis of D-methyl-2-chloropropionate: dropwise adding thionyl chloride into the mixed solution of the L-methyl lactate and pyridine, carrying out vacuum stirring, increasing the temperature to 55-90 DEG C, reacting for 1-5h, reducing the temperature to 25-35 DEG C, exhausting air, washing and separating, wherein the L-methyl lactate and the thionyl chloride are used as raw materials and the pyridine is used as a catalyst; (2) the synthesis of D-2-chloropropionic acid: hydrolyzing methyl-2-chloropropionate under the action of a sodium hydroxide solution, and carrying out chloroform extraction; and (3) the synthesis of D-2-chloropropionyl chloride: dropwise adding the thionyl chloride into the mixed solution of D-2-chloropropionic acid and the catalyst, increasing the temperature to 70-80 DEG C, reacting for 3-5 hours, and carrying out vacuum rectification to obtain a target product. The process path has the advantages that raw materials are easily available; synthesis steps are simple, safe and reliable; the waste gas generated in the production can be easily disposed; therefore, the process path is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing high-purity organic synthesis intermediate D-2-chloropropionyl chloride. Background technique [0002] Chloropropionyl chloride is an important intermediate in the synthesis of amino acid derivatives-glutamine dipeptide, mainly used in the human health industry, and is an ideal substitute for the most abundant amino acid-glutamine in the human body. Compared with glutamine, the solubility of glutamic dipeptide is 20 times that of glutamine, and it is also very stable in storage and heat sterilization. It can be directly prepared into infusion preparations for clinical use. Long-term intravenous infusion of glutamic dipeptide in healthy people does not have any side effects and Adverse reactions do not affect normal renal function. In the known technology, the existing synthetic method of D-2 chloropropionyl chloride is to use food-grade L-lactic acid and thionyl chloride to obtain D-2 chloropropionyl ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C53/50C07C51/60
Inventor 李家全马崇雷郑庚修王光政
Owner SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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