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The synthetic method of alpha ethyl ester derivative

A synthesis method and compound technology, applied in the field of synthesis of ethyl alpha ester derivatives, can solve the problems of low yield, long synthesis steps, harsh conditions, etc.

Active Publication Date: 2012-02-08
CHONGQING HUAPONT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, there are many disadvantages in the synthesis method of the compound of formula I, such as the methods disclosed in patents US4584382 and US4639459 have long synthesis steps, complex separation of chiral isomers, and low yield
Moreover, low temperature reaction (-60°C) is required, and the conditions are harsh, which is not conducive to industrial production

Method used

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  • The synthetic method of alpha ethyl ester derivative
  • The synthetic method of alpha ethyl ester derivative
  • The synthetic method of alpha ethyl ester derivative

Examples

Experimental program
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Effect test

Embodiment 8

[0053] Embodiment 8 formula I compound (R 1 is methyl, R 2 for the synthesis of ethyl)

[0054] Formula II compound (R 1 Methyl) 178.7g (0.500mol), ethyl acrylate 388ml (3.626mol), triphenylphosphine 40g (0.152mol), triethylamine 200ml (1.384mol), palladium acetate 5g (22.5mmol), N-methyl Base pyrrolidone 1000ml, heat up to 140-150°C, stir for 8h-10h. According to Example 1, 153 g (0.4229 mol) of the title compound was obtained as a brown solid, with a yield of 84.6% and a content detected by HPLC of 97.8%.

[0055] Embodiment 9 formula I compound (R 1 is methyl, R 2 for the synthesis of ethyl)

[0056] Formula II compound (R 1 Methyl) 178.7g (0.500mol), ethyl acrylate 107ml (1.000mol), triphenylphosphine 57.7g (0.22mol), triethylamine 100ml (0.692mol), palladium acetate 4.9g (22.0mmol), DMA 1000ml, heat up to 140-150°C, stir for 8h-10h. According to Example 1, 141 g (0.3897 mol) of the title compound was obtained as a brown solid, with a yield of 77.9% and a content ...

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Abstract

The synthesis method of the compound of formula I uses the compound of formula II and acrylate as raw materials, and reacts in the presence of palladium catalyst, triphenylphosphine and organic amine.

Description

Technical field: [0001] The present invention relates to the synthetic method of alpha ethyl ester derivative. Background technique: [0002] The alfa ethyl ester compound (I) is the precursor of the drug alfastin, which can be hydrolyzed and deesterified to obtain the alfastin. [0003] In the prior art, there are many disadvantages in the synthesis method of the compound of formula I, for example, the methods disclosed in patents US4584382 and US4639459 have long synthesis steps, complex separation of chiral isomers, and low yield. Moreover, low-temperature reaction (-60° C.) is required, and the conditions are harsh, which is unfavorable for industrial production. Invention content: [0004] The purpose of the invention is to provide a new synthetic method of ethyl alpha esters, overcome the deficiencies in the prior art, short synthetic steps, mild production conditions, high product purity, high yield, beneficial to industrial production. [0005] The structure of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/55
Inventor 唐朝军陈小舟
Owner CHONGQING HUAPONT PHARMA
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