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Method for splitting ibuprofen

A technology for the resolution of ibuprofen methyl ester, which is applied in the field of resolution of the compound ibuprofen [2-propionic acid], can solve the problem that the optical purity of d-ibuprofen is difficult to reach the ideal level, the operation is cumbersome, and the yield Low efficiency and other problems, to achieve the effect of reducing the pollution of "three wastes", high reaction yield and good thermal stability

Active Publication Date: 2011-09-07
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there have been many reports on the resolution of ibuprofen, but most of them use L-lysine, octylglumine, meglumine, etc. as resolution reagents, and carry out multiple recrystallizations in organic solvents to prepare dextromethorphan. Ibuprofen has cumbersome operation and low yield, and the optical purity of D-ibuprofen is difficult to reach the ideal level

Method used

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  • Method for splitting ibuprofen
  • Method for splitting ibuprofen

Examples

Experimental program
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Embodiment 1

[0034] The preparation of embodiment 1 S (+)- ibuprofen methyl ester

[0035] Dissolve 22g (100mmol) of racemic ibuprofen methyl ester and 5.9g (80mmol) of n-butanol in 400mL of dioxane, then add 10g of Novozym 435, and shake at 39°C for 20h. After the reaction, the immobilized enzyme was filtered off. The filtrate is distilled and concentrated to 30 to 50mL, separated on a silica gel column (eluent is isopropyl ether) to obtain about 10g of S(+)-ibuprofen methyl ester, and the yield is about 91% (based on S(+)-buprofen profen methyl ester).

Embodiment 2

[0036] The preparation of embodiment 2 S (+)- ibuprofen methyl ester

[0037] Dissolve 22g (100mmol) of racemic ibuprofen methyl ester and 5.9g (80mmol) of n-butanol in 400mL of dioxane, then add 10g of Novozym 435 (recovered from Example 1), and shake at 39°C for 22h . After the reaction, the immobilized enzyme was filtered off. The filtrate is distilled and concentrated to 30 to 50mL, separated on a silica gel column (eluent is isopropyl ether) to obtain about 10g of S(+)-ibuprofen methyl ester, and the yield is about 91% (based on S(+)-buprofen profen methyl ester).

Embodiment 3

[0039] Dissolve 22g (100mmol) of racemic ibuprofen methyl ester and 59g (800mmol) of n-butanol in a mixture of 500mL of methyl tert-butyl ether and petroleum ether (1:1 by volume), then add 10g of Novozym 435 , Shake the reaction at 0°C for 72h. After the reaction, the immobilized enzyme was filtered off. The filtrate is distilled and concentrated to 30 to 50ml, separated on a silica gel column (eluent is isopropyl ether) to obtain about 8g of S(+)-ibuprofen methyl ester, and the yield is about 92.7% (based on S(+)-buprofen profen methyl ester).

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Abstract

The invention relates to a method for splitting S(+)-ibuprofen shown in the split formula I. The method comprises the following steps: 1) performing an asymmetric ester exchange reaction with alcohol by taking (R, S)-methyl ibuprofen as a raw material and an immobilized lipase as a catalyst, and performing post-treatment to obtain S(+)-methyl ibuprofen; and 2) hydrolyzing the S(+)-methyl ibuprofen obtained in the step 1) in the catalysis of inorganic acid to obtain S(+)-ibuprofen. The raw materials in the preparation method provided by the invention are easily available, the yield is high, the optical purity of products is high, the pollution is low, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a resolution method of the compound ibuprofen [2-(4-isobutylphenyl) propionic acid]. It belongs to the field of chemical industry and chemical medicine. Background technique [0002] S(+)-ibuprofen [S(+)-ibuprofen] is the general name of S(+)-2-(4-isobutylphenyl)propionic acid, and its structural formula is: [0003] [0004] Molecular formula: C 13 h 18 o 2 [0005] Molecular weight: 206.28 [0006] Ibuprofen is a non-steroidal anti-inflammatory and analgesic drug. Compared with aspirin, it has stronger antipyretic, anti-inflammatory and analgesic effects, and its side effects are much smaller. It has been on the market since the late 1970s. Ibuprofen has gained rapid development. Now it has become one of the anti-inflammatory, antipyretic and analgesic drugs with the largest production and usage. Dexibuprofen is the optical isomer of the S configuration of ibuprofen. A large number of studies have shown that Dexib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/40C07C57/30C07C51/09
Inventor 孙建华刘慧敏江立新李立标
Owner BENGBU BBCA MEDICINE SCI DEV
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