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Synthetic method of intermediate cyclopropyl acetylene of anti-aids drug efavirenz

A technology of cyclopropyl acetylene and efavirenz, which is applied in the field of synthesis of intermediate cyclopropyl acetylene, can solve the problems of unsuitability for industrialized production, complicated process, troublesome operation and the like, and achieves convenient operation, simple process and cost reduction. Effect

Inactive Publication Date: 2014-03-26
JIUJIANG ZHONGTIAN PHARMA
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  • Summary
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AI Technical Summary

Problems solved by technology

Existing technology at home and abroad mainly contains 3 kinds of synthetic methods that take cyclopropylmethylaldehyde, 5-chloro-1-pentyne and other alkynyl-containing compounds as raw materials; but these four synthetic methods are complicated in process and troublesome in operation. High cost, many wastes, not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Step 1: The ratio of cyclopropanone: phosphorus pentachloride is 1:1.2, and the ratio of cyclopropanone (42.0g, 0.5mol): phosphorus pentachloride (125.1g, 0.6mol), organic solvent Be xylene 336g, its consumption is 8 times of cyclopropanone.

[0015] Step 2: Add phosphorus pentachloride and organic solvent into a 500ml four-necked bottle, start stirring, cool to -15°C, add cyclopropylmethanone dropwise, after the dropwise addition, keep warm at this temperature for 8 hours, the reaction is over, and the ice melts , Layered to obtain 59g α, α-dichloroethyl cyclopropane, yield 85%.

[0016] step two

[0017] Add 120g of 30% potassium hydroxide aqueous solution into a 250ml four-necked bottle, start stirring, add 0.6g of tetrabutylammonium bromide, then add 30g of α,α-dichloroethylcyclopropane, and react at 75-80°C for 10 -12 hours, distillation promptly obtains product 16g, and yield is 89%.

Embodiment 2

[0019] Step 1: The ratio of the amount of the feed material to cyclopropanone: phosphorus pentachloride is 1:1.4, and the feed, cyclopropanone (21.0g, 0.25mol): phosphorus pentachloride (80g, 0.35mol), the organic solvent is Normal hexane 210g, its consumption is 10 times of cyclopropanone.

[0020] Step 2: Add phosphorus pentachloride and organic solvent into a 500ml four-necked bottle, start stirring, cool to -12°C, add cyclopropylmethanone dropwise, after the dropwise addition, keep warm at this temperature for 8 hours, the reaction is over, and the ice melts , Layered to obtain 29g α, α-dichloroethyl cyclopropane, yield 83%.

[0021] Add 100g of 50% sodium hydroxide aqueous solution into a 250ml four-necked bottle, start stirring, add 0.1g of tetrabutylammonium bromide, then add 25g of α,α-dichloroethylcyclopropane, and react at 75-80°C for 10 -12 hours, distillation promptly obtains product 14g, and yield is 93%.

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Abstract

The invention discloses a synthetic method of intermediate cyclopropyl acetylene of an anti-aids drug efavirenz, and relates to the technical field of synthesis of cyclopropyl acetylene. The synthetic method comprises the following steps: reacting in an organic solvent to produce alpha, alpha-ethyl dichloride cyclopropane by taking cyclopropyl methyl ketone as a raw material and taking phosphorus pentachloride as a chlorinating agent; and obtaining the cyclopropyl acetylene by adding the alpha, alpha-ethyl dichloride cyclopropane into strong base aqueous liquor through a phase transfer catalyst. The synthetic method has the beneficial effects that the organic solvent and inorganic strong base are not needed to be adopted, expensive reagents such as the organic solvent and potassium tert-butoxide are avoided; moreover, process raw materials are easily available, process is simple, operation is convenient, cost is lowered and the three wastes are reduced, and therefore, the synthetic method is suitable for industrial production.

Description

[0001] Technical field: [0002] The invention relates to the technical field of synthesis of cyclopropylacetylene, in particular to a method for synthesizing an intermediate cyclopropylacetylene of the anti-AIDS drug Efluverenz. Background technique: [0003] Cyclopropylacetylene (CPA) is a key intermediate of the anti-AIDS drug Efluverenz, for example, a reverse transcriptase inhibitor DMP-266 can be synthesized[1,2]. Cyclopropylacetylene, as an important synthon of the cyclopropyl skeleton of such drug molecules, soon became the research focus of many research groups and research units. Existing technology at home and abroad mainly contains 3 kinds of synthetic methods that take cyclopropylmethylaldehyde, 5-chloro-1-pentyne and other alkynyl-containing compounds as raw materials; but these four synthetic methods are complicated in process and troublesome in operation. The cost is high, and there are many three wastes, so it is not suitable for industrial production. I...

Claims

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Application Information

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IPC IPC(8): C07C13/04C07C1/30
Inventor 叶仙春陈少兵段方林
Owner JIUJIANG ZHONGTIAN PHARMA
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