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Industrialization preparing method for 3-propyl-ethylene oxide-2-carbonyl cyclopropanecarboxamide

A technology of carbonyl cyclopropanamide and ethylene oxide, which is applied in the field of industrial preparation of 3-propyl-oxirane-2-carbonyl cyclopropanamide, can solve the problems of difficult to meet market demand, difficult to purchase in large quantities, and production cost Advanced problems, to achieve the effect of convenient operation, mild reaction conditions, and easy-to-obtain materials

Inactive Publication Date: 2017-03-29
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw material in "Route 1" is trans-2-hexenoic acid, which is expensive and difficult to purchase in large quantities, resulting in high production costs of 3-propyl-oxirane-2-carbonyl cyclopropanamide, which is difficult to meet the market need

Method used

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  • Industrialization preparing method for 3-propyl-ethylene oxide-2-carbonyl cyclopropanecarboxamide

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Effect test

Embodiment 1

[0035] An industrial preparation method of 3-propyl-oxirane-2-carbonyl cyclopropanamide, using malonic acid as a starting material, is realized through the following steps:

[0036] (1) Preparation of hexenoic acid

[0037] Put 38kg of pyridine and 2.39kg of diethylamine into the reaction kettle, open the circulating water, add 50kg of malonic acid, control the temperature below 40°C, add 35.34kg of n-butyraldehyde dropwise, control the temperature within 50°C during the period, after the dropwise addition Stir at room temperature for 15 hours, evaporate diethylamine under reduced pressure at 90°C, and lower the temperature. When the temperature drops to about 50°C, add 42kg of toluene and continue to cool down to below 20°C; add 53.2kg of 50% hydrochloric acid dropwise, during which the temperature is controlled at 25°C Within, until the pH value of the reaction solution reaches 1, evaporate to dryness under reduced pressure to obtain the crude product of hexenoic acid, cool ...

Embodiment 2

[0046] An industrial preparation method of 3-propyl-oxirane-2-carbonyl cyclopropanamide, using malonic acid as a starting material, is realized through the following steps:

[0047] (1) Preparation of hexenoic acid

[0048] Put 152kg of pyridine and 9.56kg of triethylamine into the reaction kettle, turn on the circulating water, add 200kg of malonic acid, control the temperature below 40°C, add 167.4kg of n-butyraldehyde dropwise, and control the temperature within 50°C during the period. Stir at room temperature for 15 hours, evaporate triethylamine under reduced pressure at 90°C, and lower the temperature. When the temperature drops to about 50°C, add 168kg of ethanol, continue to cool down to below 20°C, and add 212.8kg of 50% phosphoric acid dropwise. During this period, the temperature is controlled at 25 Within ℃, until the pH value of the reaction solution reaches about 3, evaporate to dryness under reduced pressure to obtain the crude hexenoic acid, cool down, and set ...

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Abstract

The invention discloses an industrialization preparing method for 3-propyl-ethylene oxide-2-carbonyl cyclopropanecarboxamide, and belongs to the field of pharmaceutical chemistry. The industrialization preparing method includes the steps that malonic acid serves as a initial raw material, malonic acid (A) is added into alkali, and then the mixture and butyric aldehyde (B) are condensed to prepare hexenic acid (C); an acylation reagent is added into the hexenic acid (C), an acylation reaction is carried out, then concentration is carried out, and hexenoyl chlorine (D) is obtained; the hexenoyl chlorine (D) and cyclopropylamine are reacted to obtain hexenoyl amine (E), the exenoyl amine (E) is subjected to an epoxidation reaction, and the 3-propyl-ethylene oxide-2-carbonyl cyclopropanecarboxamide is obtained. According to the industrialization preparing method, the malonic acid is used as a raw material; compared with the traditional technology, the materials are easy to obtain, the cost is only about 20% of the cost of 'a first path', the cost is greatly reduced, the yield is higher, is 90% or above, and is increased by 15% or above compared with the yield of 'the first path' and increased by 30% or above compared with the yield of 'a second path', the reaction condition is more mild, operating is more convenient, and the requirements of mass industrialization production can be met.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an industrial preparation method of 3-propyl-oxirane-2-carbonyl cyclopropanamide. Background technique [0002] 3-propyl-oxirane-2-carbonyl cyclopropanamide, its structural formula is as shown in I, [0003] , [0004] It is an important intermediate for the preparation of the antiviral drug Telaprevir, which is an effective drug for treating hepatitis C. [0005] Hepatitis C virus (HCV) infection has become a serious threat to public health. Human infection with HCV can lead to chronic liver necrosis and fibrosis, and some can develop into liver cirrhosis and even liver cancer. Globally, the seroprevalence rate of HCV is about 3%. In the United States alone, there may be nearly 4 million people infected with HCV, and the number of HCV infected people in China is about 40 million. Telaprevir is a new type of serine protease inhibitor developed by Vertex Pharmaceuticals in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12C07D303/48
CPCC07D301/12C07D303/48
Inventor 袁伟成郑宁川付艺巍周鸣强徐小英
Owner CHENGDU LIKAI CHIRAL TECH
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