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Method for preparing 5(S)-aminomethyl-3-aryl-2-oxazolidinone

A technology of oxazolidinones and aminomethyl groups, which is applied in the field of preparation of 5-L-aminomethyl-3-aryl-2-oxazolidinones, and can solve problems affecting optical purity, long reaction time, and temperature It is not suitable for problems such as excessively high, and achieves the effects of low cost, high total yield, and easy recovery and purification

Inactive Publication Date: 2012-01-11
OMEGA MEDICAL TAIWAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of the compound L-glycidyl phthalimide (I) has been disclosed in EP1403267A1 in 2004, and this method is to utilize potassium phthalimide (potassium phthalimide) / (PhCH 2 ) Me 3 NCl / racemic epichlorohydrin (racemic epichlorohydrin) or right-handed epichlorohydrin ((R)-epichlorohydrin) or left-handed epichlorohydrin ((S)-epichlorohydrin) can be prepared by reacting in a solvent Rotary L-glycidyl phthalimide (I) or L-glycidyl phthalimide (I) with (R) or (S) optical activity, the disadvantage of this method is The reaction time is too long (at least one day) and the temperature should not be too high, otherwise it will affect the optical purity

Method used

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  • Method for preparing 5(S)-aminomethyl-3-aryl-2-oxazolidinone

Examples

Experimental program
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Effect test

Embodiment 1

[0025] The preparation method of L-glycidylphthalimide ((S)-glycidylphthalimide) (I):

[0026]Weigh potassium phthalimide (Potassium phthalimide) (8.01g, 43.25mmol) and place it in a double-neck flask, add (S)-Epichlorohydrin (10ml, 127.5mmol) and tetrabutyl Ammonium bromide (1.2g, 3.727mmol) (suspended as light yellow solid) was reacted at 30°C for 5.5 hours. After the reaction was finished, add 80ml of water and 80ml of ethyl acetate, extract, separate layers, extract the organic layer with 320ml of saturated brine, and dissolve with anhydrous magnesium sulfate (MgSO 4 ) was dried, filtered, and the filtrate was concentrated to dryness, and the resulting solid was dried with oil-free pumping for 16 hours to obtain 7.3 g of solid L-glycidyl phthalimide (I). The optical purity was 87% ee.

[0027] 1 H-NMR (deuterated chloroform, CDCl 3 ):

[0028] 2.65(dd, J=4.8Hz, 2.5Hz, 1H), 2.78(dd, J=4.8Hz, 2.5Hz, 1H), 3.21(m, 1H), 3.78(dd, J=14.4Hz, 5.0Hz, 1H ), 3.93(dd, J=14.4Hz, 5...

Embodiment 2

[0039] The preparation method of L-glycidyl phthalimide (I): embodiment is the same as Example 1, only benzyltrimethylammonium chloride is replaced with tetrabutylammonium bromide to obtain 7.5g solid L-phthalimide Oxypropylphthalimide (I). The optical purity is 98% ee.

Embodiment 3

[0041] The preparation method of L-glycidyl phthalimide (I): the embodiment is the same as in Example 1, only benzyltrimethylammonium chloride is replaced with tetrabutylammonium bromide, and the reaction solvent is Virahol simultaneously 7.7 g of solid L-glycidylphthalimide (I) were obtained. The optical purity is 98.3%ee.

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Abstract

The invention discloses a method for preparing 5(S)-aminomethyl-3-aryl-2-oxazolidinone. The method comprises the following steps of: reacting (S)-glycidyl phthalimide and aryl aniline to prepare an addition compound; and finally preparing the 5(S)-aminomethyl-3-aryl-2-oxazolidinone through cyclization reaction and aminolysis reaction. The method has the advantages of high total yield and low cost; all intermediates and a product synthesis method have the characteristics of convenience in recovery and purification; and the purity of a final product of the method is at least over 99.9 percent.

Description

technical field [0001] The invention relates to a method for preparing 5-L-aminomethyl-3-aryl-2-oxazolidinones (5(S)-Aminomethyl-3-Aryl-2-Oxazolidinone). Background technique [0002] 5-L-aminomethyl-3-aryl-2-oxazolidinones (5(S)-Aminomethyl-3-Aryl-2-Oxazolidinones) (A) derivatives have been successfully used in anti-infective drugs and cardiology Vascular drugs and anticoagulants, especially the marketed anti-infective drug Linezolid and the oral coagulant rivaroxaban. [0003] About the synthetic method of this type of 5-left-handed-aminomethyl-3-aryl-2-oxazolidinones (A) [0004] [0005] Mainly convert 5-hydroxymethyl substituted oxazolidinones (5-hydroxymethyl substituted oxazolidinones) into 5-L-aminomethyl-3-aryl-2-oxazolidinones (A) such as WO2007 / 064818; WO95 / 07271; US5688792 (1997); J.Med.chem.39,673 (1996), etc., all utilize n-BuLi to react at -78°C, which is not suitable for industrial production, while WO01 / 47919A1 reacts There are also some shortcomings i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/20C07D413/10C07D413/14
CPCC07D263/20C07D413/10C07D413/14
Inventor 施凯翔林惠英谢幼容刘清维
Owner OMEGA MEDICAL TAIWAN
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