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Method for detecting content of (1R, 2R)-diaminocyclohexane

A technology of cyclohexanediamine and a determination method, which is applied in the field of high-performance liquid phase method detection, and can solve the problems of method error and low precision.

Active Publication Date: 2010-06-23
SHANGHAI ACEBRIGHT PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, due to the special physical and chemical properties of (1R, 2R)-cyclohexanediamine, there are certain difficulties in the determination of its content and optical purity. The current detection method only relies on the detection of specific rotation and melting point to determine the content. The error of the method is very large, and the accuracy is not high.

Method used

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  • Method for detecting content of (1R, 2R)-diaminocyclohexane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of reference substance:

[0024] Dichloromethane (20ml) was added to (S)-naproxen (2.3g), and cooled to 0°C in an ice-water bath. Dicyclohexylcarbodiimide (0.7 g) was added and reacted for 10 minutes. Add (1R,2R)-cyclohexanediamine (0.3g) and N,N-dimethylaminopyridine (0.03g), naturally warm to room temperature, and stir overnight. After the obtained reaction product was filtered to remove the solid, the solid obtained after concentrating the filtrate was prepared and separated by a high performance liquid phase instrument to obtain (1R, 2R)-cyclohexyl-bis[(6'-methoxyl)-2"(S )-Naphthylisopropyl]amide, ms(M+1): 539, optical purity 99.8%.

[0025] A control sample of (1S,2S)-cyclohexyl-bis[(6'-methoxy)-2"(S)-naphthaleneisopropyl]amide can be obtained by a similar method, with an optical purity of 99.3%.

Embodiment 2

[0027] Dichloromethane (40ml) was added to (R)-mandelic acid (3.0g), and cooled to 0°C in an ice-water bath. Diisopropylcarbodiimide (0.9 g) was added and reacted for 10 minutes. Add (1R,2R)-cyclohexanediamine (0.6g) and N,N-dimethylaminopyridine (0.06g), naturally warm to room temperature, and stir overnight. After the obtained reaction product is filtered to remove the solid, the solid obtained after concentrating the filtrate is prepared and separated by a high performance liquid phase instrument to obtain (1R, 2R)-cyclohexyl-bis[(2'(R)-hydroxyl)phenethyl]amide The control sample of the same, ms(M+1): 383, optical purity 99.5%.

[0028] A control sample of (1S,2S)-cyclohexyl-bis[(2'(R)-hydroxy)phenethyl]amide can be obtained by a similar method, with an optical purity of 99.3%.

Embodiment 3

[0030] Add (S)-naproxen (2.3 g) into dichloromethane (20 ml), and cool to 0° C. in an ice-water bath. Dicyclohexylcarbodiimide (1.4 g) was added and reacted for 10 minutes. Add self-made (1R,2R)-cyclohexanediamine (0.5g), N,N-dimethylaminopyridine (0.03g), naturally warm up to room temperature, stir overnight, the resulting product is directly analyzed by HPLC, the content is 98.1 %, the optical purity is 98.0%.

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Abstract

The invention provides a method for detecting the content of (1R, 2R)-diaminocyclohexane, which comprises the following steps of: in the presence of catalysis amount of an organic basic catalyst, under the action of a condensing agent, condensing the 1,2-diaminocyclohexane and a chiral organic acid in an organic solvent; directly detecting a solution obtained after the condensation by using a high-efficiency liquid phase instrument; or filtering solids out of a condensation product firstly, and then detecting solid matters obtained after concentrating filtrate by using the high-efficiency liquid instrument. The invention has simple operation method, low cost, good liquid phase separation effect on an enantiomer and high separation degree more than 2.0.

Description

technical field [0001] The invention relates to detecting the content of (1R, 2R)-cyclohexanediamine in 1,2-cyclohexanediamine by a high performance liquid phase method. Background technique [0002] (1R,2R)-cyclohexanediamine, as a chiral synthesis reagent, plays an important role in the fields of organic chemistry and medicine. One of the important uses is as an important raw material of the third generation platinum anticancer drug oxaliplatin, and its optical purity directly determines the optical purity of oxaliplatin, so in industrial production for (1R , 2R)-the detection of the content and optical purity of cyclohexanediamine has become a key issue. [0003] However, due to the special physical and chemical properties of (1R, 2R)-cyclohexanediamine, there are certain difficulties in the determination of its content and optical purity. The current detection method only relies on the detection of specific rotation and melting point to determine the content. The error...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02B01J20/29
Inventor 李金亮蔡志刚任安平
Owner SHANGHAI ACEBRIGHT PHARMA CO LTD