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Method for synthesizing optically active laevogyrate and dexiotropous camphor sulfonic acid

A technology of D-camphorsulfonic acid and optical activity, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as difficult separation of L-isomer, poor optical purity, complicated process, etc., and achieve low cost, The effect of less waste and simple process

Inactive Publication Date: 2007-12-26
上海康福赛尔医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Optically active camphorsulfonic acid is an important resolving agent for optically active amino acid drugs. At present, the optically active camphorsulfonic acid only has the dextrorotatory form, which is obtained by sulfonating natural camphor. With the development of chiral drugs, the application of L-camphorsulfonic acid is becoming more and more extensive, but at present, the separation of L-camphorsulfonic acid is difficult, the process is complicated, the optical purity is poor, the cost is high, and the pollution is serious.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A preparation method for optically active left-handed and right-handed camphorsulfonic acid comprises the following steps: 1. Preparation of racemic sulfonic acid: add 100 kilograms of 98% acetic anhydride and 20 kilograms of acetic acid in a 200-liter enamelled reactor with stirring, Add 75 kg of racemic camphor under stirring and cooling, cool down to 0-5°C, add 55 kg of 98% sulfuric acid, then keep the temperature at 5-30°C, react for 60 hours, cool to -2-5°C after the reaction, and keep for 15 hours. Centrifugal filtration, washing with acetic acid, and drying in vacuo gave 70 kg of white crystalline racemic camphorsulfonic acid, with a weight yield of 93%;

[0017] Two, the preparation of left-handed and right-handed camphorsulfonic acid, 1 resolution: add 23.2 kilograms of racemic camphorsulfonic acid while stirring in 100 liters of enamel kettles, 18 kilograms of resolving agent compositions, 20 kilograms of water, mixing is heated to 1 hour at 60-100°C, cool to ...

Embodiment 2

[0020] A preparation method for optically active left-handed and right-handed camphorsulfonic acid comprises the following steps: 1. Preparation of racemic sulfonic acid: 120 kilograms of 98% acetic anhydride and 10 kilograms of acetic acid are added in a 200-liter enamelled reactor with stirring, Add 75 kg of racemic camphor under stirring and cooling, cool down to 5-15°C, add 50 kg of oleum, then keep the temperature at 15-30°C, react for 48 hours, cool to 0-5°C after reaction, keep for 15 hours, and centrifugally filter , washed with acetic acid, and vacuum-dried to obtain 75 kg of white crystal racemic camphorsulfonic acid, with a weight yield of 100%;

[0021] Two, the preparation of left-handed and right-handed camphorsulfonic acid, 1 resolution: add 23.2 kilograms of racemic camphorsulfonic acid while stirring in 100 liters of enamel kettles, 15 kilograms of resolving agent compositions, 20 kilograms of water, mixing is heated to 1 hour at 60-100°C, cool to 5-10°C, keep...

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Abstract

This invention relates to a method for preparing optically active L-camphor sulfonic acid and D-camphor sulfonic acid. The method comprises: preparing acetic anhydride 100 parts, acetic acid 8-20 parts, racemic camphor 60-80 parts, and fuming sulphuric acid 40-60 parts, synthesizing racemic camphor sulfonic, resolving, and puridying to obtain the products. The method has such advantages as little waste discharge, little pollution; simple process and can separate L-camphor sulfonic acid and D-camphor sulfonic acid by using one resolution agent. The products have high optical activity and high resolution yield (near 100%).

Description

technical field [0001] The invention relates to a preparation method of camphorsulfonic acid, in particular to a preparation method of optically active left-handed and right-handed camphorsulfonic acid. Background technique [0002] Optically active camphorsulfonic acid is an important resolving agent for optically active amino acid drugs. At present, the optically active camphorsulfonic acid only has the dextrorotary form, which is obtained by sulfonating natural camphor. With the development of chiral drugs, the application of L-camphorsulfonic acid is becoming more and more extensive. However, at present, the separation of L-camphorsulfonic acid is difficult, the process is complicated, the optical purity is poor, the cost is high, and the pollution is serious. Contents of the invention [0003] Purpose of the present invention is exactly a kind of production method that provides in order to overcome the defective that above-mentioned technology exists, and optical puri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/44C07C309/25
Inventor 沈洪明
Owner 上海康福赛尔医药科技有限公司
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