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The synthetic method of dichloroacetate

A technology of dichloroacetate and synthesis method, which is applied in the field of compound synthesis, can solve the problems that cannot be used as raw material medicine, product quality is uncontrollable, and the synthesis process does not conform to the production process of raw material medicine, so as to achieve controllable quality and easy operation simple effect

Inactive Publication Date: 2011-12-14
赵永俊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many methods for preparing dichloroacetate in the prior art, but what these methods prepare are basically chemical grade dichloroacetate, rather than pharmaceutical grade, dichloroacetate on the market Acetate is mostly a fine chemical product, and its production process and synthesis process do not meet the production process requirements of raw materials, and the product quality is uncontrollable. At the same time, most of them contain many unknown impurities and substances harmful to human body, so they cannot be used as raw materials

Method used

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  • The synthetic method of dichloroacetate
  • The synthetic method of dichloroacetate
  • The synthetic method of dichloroacetate

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Synthesis of Sodium Dichloroacetate

[0027] Step 1.1 Esterification of 2,2'-dichloroacetyl chloride with 9-fluorenylmethanol to obtain fluorenylmethyl dichloroacetate

[0028] Add 5.00 g of 9-fluorenemethanol and 4.51 g of 2,2'-dichloroacetyl chloride to 20 ml of toluene solution, mix and heat to 110°C for 2 hours under reflux. After the reaction is complete as detected by TLC, the reaction solution is placed in After vacuum concentration at 70°C, 10 ml of toluene was added for concentration, and finally a solid crude product was obtained.

[0029] The obtained above crude product was crystallized at 55°C in 50 ml of acetone and petroleum ether mixed solvent with a volume ratio of 1:9 to obtain 6.01 g of the formula The compound, fluorenylmethyl dichloroacetate. After concentrating and recrystallizing the mother liquor, 0.69g of formula The compound, the yield is 86%.

[0030]

[0031] Electrospray mass spectrometry characterization data is: 306+23...

Embodiment 2

[0040] Synthesis of ammonium dichloroacetate

[0041] Step 2.1 Esterification of 2,2'-dichloroacetyl chloride with 9-fluorenylmethanol to obtain fluorenylmethyl dichloroacetate

[0042] Add 5.00 g of 9-fluorenylmethanol and 4.51 g of 2,2'-dichloroacetyl chloride to 20 ml of toluene solution, mix and heat to 110°C for 2 hours under reflux. After the reaction is detected by TLC, the reaction solution is placed in After vacuum concentration at 70°C, and then adding 10 ml of toluene to concentrate, a solid crude product was obtained.

[0043] The obtained above crude product was crystallized at 55°C in 50 ml of acetone and petroleum ether mixed solvent with a volume ratio of 1:9 to obtain 6.01 g of the formula The compound, fluorenylmethyl dichloroacetate. After concentrating and recrystallizing the mother liquor, 0.69g of formula The compound, the yield is 86%.

[0044]

[0045] Electrospray mass spectrometry characterization data is: 306+23 (Na + ), see ...

Embodiment 3

[0054] Synthesis of Calcium Dichloroacetate

[0055] Step 3.1 Esterification of 2,2'-dichloroacetyl chloride with 9-fluorenylmethanol to obtain fluorenylmethyl dichloroacetate

[0056] Add 5.00 g of 9-fluorenylmethanol and 4.51 g of 2,2'-dichloroacetyl chloride to 20 ml of toluene solution, mix and heat to 110°C for 2 hours under reflux. After the reaction is detected by TLC, the reaction solution is placed in After concentrated in vacuo at 70°C, and concentrated by adding 10 ml of toluene, a crude solid product was obtained.

[0057] The obtained above crude product was crystallized at 55°C in 50ml of a mixed solvent of acetone and petroleum ether with a volume ratio of 1:9 to obtain 6.01g of the formula The compound, fluorenylmethyl dichloroacetate. After concentrating and recrystallizing the mother liquor, 0.69g of formula The compound, the yield is 86%.

[0058]

[0059] Electrospray mass spectrometry characterization data is: 306+23 (Na + ), see ...

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Abstract

The invention provides a synthetic method of dichloroacetate bulk medicinal chemicals, comprising the following steps: (a) 2,2'- dichloroacetylchloride (formula I) and 9- fluorenylmethanol (formula II) are subject to esterification to obtain fluorenylmethyl dichloroacetate (formula III); (b) the obtained fluorenylmethyl dichloroacetate is subject to hydrolysis reaction to obtain the crude product of 2,2'- dichloroacetate (formula IV); and (c) the obtained crude product of 2,2'- dichloroacetate is subject to recrystallization to obtain 2,'2- dichloroacetate with the purity of more than 99.5%. The synthesis method provided by the invention is simple, the quality of the products is controllable, and the prepared dichloroacetate can satisfy the standard of bulk medicinal chemicals and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of compound, more particularly relate to a kind of synthetic method of dichloroacetate crude drug. Background technique [0002] As an experimental drug, dichloroacetate has been used in more than 40 clinical studies on hereditary mitochondrial lactic acidosis, diabetes and acute myocardial ischemia. Studies have shown that it has significant therapeutic effects on cardiovascular and metabolic diseases, and has obvious inhibitory effects on cancers, such as lung cancer, glioma, and breast cancer. At present, there are many methods for preparing dichloroacetate in the prior art, but what these methods prepare are basically chemical grade dichloroacetate, rather than pharmaceutical grade, dichloroacetate on the market Acetate is mostly a fine chemical product, and its production process and synthesis process do not meet the production process requirements of raw materials. The product quality i...

Claims

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Application Information

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IPC IPC(8): C07C53/16C07C51/41A61P35/00
Inventor 赵永俊
Owner 赵永俊
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