Chiral intermediate (S, S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide or its salt and preparation method thereof

A technology of hydroxycaproylamide and cyclopropyl, applied in the field of preparation of chiral intermediate (S,S)-3-amino-N-cyclopropyl-2-hydroxycaproylamide or its salt, can solve the problem Stability, difficult crystallization and other problems, to achieve high yield, low cost, and reduce energy consumption

Inactive Publication Date: 2012-09-12
PORTON FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The object of the present invention is to provide a method for preparing compound (S, S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide or its salt, which can

Method used

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  • Chiral intermediate (S, S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide or its salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 1.5 g of water and 30 g of the compound of formula II into a 250 ml three-necked reaction flask, then add 23 g of D-tartaric acid and 90 ml of ethanol, add 40 ml of acetic acid under stirring, heat up and reflux for about 2 hours, then cool down to 25-30°C and stir for crystallization. After filtering, the filter cake was soaked in ethanol, then filtered, and dried to constant weight to obtain 22.3 g of the crude compound of formula III as a white solid, EE: 87.2%, yield: 41%.

[0029]

Embodiment 2

[0031] Add 22.3g of the crude compound of formula III obtained in the example into a mixed solution of 100ml of ethanol and 12ml of water, stir and raise the temperature to 60-65°C, then keep it warm for 45 minutes, then cool down to 20-25°C, crystallize, filter, and the mother liquor Save it for later use, wash the filter cake, and dry to obtain 17.5 g of the fine compound of formula III, EE: 99.8%, and the yield is 79%.

[0032] The product in the above mother liquor was recovered to obtain 2 g of the refined compound of formula III, EE: 99.9%.

Embodiment 3

[0034] Add 30g of the compound represented by formula III to a 1L four-necked reaction flask, then add 490g of chloroform, control the temperature at 20-25°C and stir for 45 minutes, filter to remove the solid, and concentrate the mother liquor to dryness at 40°C under a pressure of -0.09MaP , to obtain the crude product of the compound shown in formula I.

[0035] The crude compound represented by formula I was added to 150 g of absolute ethanol, heated to 50-55° C. and stirred for 1 hour, then cooled to 20-25° C. for crystallization, and filtered to obtain the refined compound represented by formula I.

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PUM

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Abstract

The invention relates to a chiral intermediate (S, S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide or its salt and a preparation method thereof. The chiral intermediate (S, S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide is an important intermediate for preparing a hepatitis C-resistant drug Telaprevir. The preparation method utilizes D-tartaric acid as a resolving agent to resolve 3-amino-N-cyclopropyl-2-hydroxyalkanamide so that the chiral intermediate (S, S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide or its salt is obtained.

Description

technical field [0001] The invention relates to a method for preparing an important intermediate (S,S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide or a salt thereof, which can be used to prepare the anti-hepatitis C drug Telaprevir, specifically, the method Using D-tartaric acid as a resolving agent to resolve 3-amino-N-cyclopropyl-2-hydroxyhexanamide to obtain (S,S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide amides or their salts. Background technique [0002] In 1974, Golafield first reported non-A non-B hepatitis after blood transfusion. In 1989, American scientist Michael Houghton (Michael Houghton) and his colleagues used a new technical method——molecular biology methods, and finally found the virus. Gene sequence, cloned hepatitis C virus, and named the disease and its virus as hepatitis C (Hepatitis C) and hepatitis C virus (HCV). Because the HCV genome is similar to human flaviviruses and pestiviruses in structure and phenotypic characteristics, it is classified as Fl...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/24
Inventor 洪武洲彭磊陈红蛟
Owner PORTON FINE CHEM
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