Recovering and applying method of clopidogrel resolving agent

A technology for clopidogrel and clopidogrel hydrochloride, applied in the field of organic chemical synthesis, can solve the problems of difficult separation of levocamphorsulfonic acid, poor optical purity, complicated process, etc., and achieves short recovery reaction time, low production cost, and optical purity. high effect

Inactive Publication Date: 2010-07-28
TIANJIN CENT PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] With the development of optically active chiral drugs, the application of camphorsulfonic acid is becoming more and more extensive. At present, the separation of L

Method used

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  • Recovering and applying method of clopidogrel resolving agent

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Experimental program
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Effect test

Embodiment 1

[0020] The mother liquor in the above reaction was adjusted to pH = 6 with sodium carbonate, crystallized at room temperature for 0.5 hours, filtered to obtain solid sodium camphorsulfonate, added 70ml (2 times) ethyl acetate, adjusted to pH = 1 with sulfuric acid, and crystallized at room temperature for 2 hours , filtered to obtain 14.5g of L-camphorsulfonic acid, mp193-195℃, [α] D =-42.9°, the recovery rate was 96.03%. It should be noted that this mother liquor was used as a raw material mother liquor for the invention described below.

Embodiment 2

[0022] The mother liquor in the above reaction was adjusted to pH = 7 with sodium bicarbonate, crystallized at room temperature for 1 hour, filtered to obtain solid sodium camphorsulfonate, added 140ml (4 times) ethyl acetate, adjusted to pH = 3 with sulfuric acid, and crystallized at room temperature 4 hour, filtered to obtain 14.9g of L-camphorsulfonic acid, mp194-195℃, [α] D =-43.5°, the recovery rate was 98.68%.

Embodiment 3

[0024] The mother liquor in the above reaction was adjusted to pH=8 with sodium carbonate, crystallized at room temperature for 2 hours, filtered to obtain solid sodium camphorsulfonate, added 70ml (2 times) ethyl acetate, adjusted to pH=5 with phosphoric acid, and crystallized at room temperature for 8 hours , filtered to obtain 13.7g of L-camphorsulfonic acid, mp193-194℃, [α] D =-41.5°, the recovery rate was 90.73%.

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Abstract

The invention discloses a recovering and applying method of camphorsulfonicacid for resolving clopidogrel, which comprises the following steps: taking resolving mother solution of racemic clopidogrel hydrochloride as a raw material; reacting the raw material with sodium bicarbonate to generate salt; reacting the salt with sulfuric acid to obtain the camphorsulfonicacid with qualified optical rotation; and resolving the clopidogrel again. The invention recovers and applies the camphorsulfonicacid in the reaction waste liquid of clopidogrel hydrogen sulfate, greatly reduces the cost, has simple industrial operation and is beneficial for industrial production on a large scale.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a method for preparing pesticides and pharmaceutical intermediates, more specifically a method for recovering and applying a clopidogrel resolution agent, that is, a method for recovering and applying camphorsulfonic acid for splitting clopidogrel . Background technique [0002] Camphorsulfonic acid is prepared from camphor through sulfonation reaction, and can be used as a pharmaceutical intermediate and an optically active body resolving agent for amino acid drugs. Sodium camphorsulfonate is a veterinary central stimulant and can also be used as a respiratory stimulant. Chemical structure: [0003] [0004] With the development of optically active chiral drugs, the application of camphorsulfonic acid is more and more extensive. At present, the separation of L-camphorsulfonic acid is more difficult than D-camphorsulfonic acid, the process is complicated, th...

Claims

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Application Information

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IPC IPC(8): C07C309/19C07C303/44
Inventor 孟庆礼杨冠宇王学元李玉梅季娟张旭婷
Owner TIANJIN CENT PHARM CO LTD
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