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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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  • 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 overcome the instability and instability of the prior art. It has disadvantages such as difficult crystallization, and is very suitable for industrial production

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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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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