Synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1, 4-oxyaza-4, 5-dicarboxylic acid

A synthetic method, tert-butyl technology, applied in the direction of organic chemistry, bulk chemical production, etc., can solve the problems of lack of reports, etc., and achieve the effects of easy operation, simplified operation process, and reasonable reaction process design

Active Publication Date: 2016-06-22
CHANGZHOU HEQUAN PHARMA CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the literature lacks reports on its industrial synthesis methods, and various derivatives with this compound as the core have important roles in organic synthesis and drug synthesis.

Method used

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  • Synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1, 4-oxyaza-4, 5-dicarboxylic acid
  • Synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1, 4-oxyaza-4, 5-dicarboxylic acid
  • Synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1, 4-oxyaza-4, 5-dicarboxylic acid

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Experimental program
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Effect test

Embodiment 1

[0014]

[0015] 200 g compound 2 Dissolve in 1.5 liters of anhydrous tetrahydrofuran solution, add 48 grams of sodium hydride in batches under ice bath, stir for 30 minutes, add 172 grams of ethyl bromoacetate reagent dropwise, and stir at room temperature for 30 minutes. TLC (petroleum ether: ethyl acetate volume ratio = 3: 1, R f =0.5) shows that the reaction is over, the reaction solution is slowly added to a saturated ammonium chloride solution to quench the reaction, extracted with ethyl acetate, the organic layer is dried by adding anhydrous sodium sulfate, filtered, and rotary evaporated under reduced pressure to obtain a yellow oil, and the crude Product, yield: 70%.

Embodiment 2

[0017]

[0018] 200 g compound 2 Dissolve in 1.5 liters of anhydrous dimethylformamide solution, add 48 grams of sodium hydride in batches under ice bath, stir for 30 minutes, add 172 grams of ethyl bromoacetate reagent dropwise, and stir at room temperature for 30 minutes. TLC (petroleum ether: ethyl acetate volume ratio = 3: 1, R f =0.5) shows that the reaction is over, the reaction solution is slowly added to a saturated ammonium chloride solution to quench the reaction, extracted with ethyl acetate, the organic layer is dried by adding anhydrous sodium sulfate, filtered, and rotary evaporated under reduced pressure to obtain a yellow oil, and the crude Product, yield: 95%.

[0019] Synthesis of ethyl 2-(2-(benzylamine)ethoxy)acetate hydrochloride

[0020]

[0021] 400 g compound 3 Dissolve in 1 liter of ethyl acetate solution, slowly add 1 liter of hydrogen chloride gas / ethyl acetate (4 mol / liter) under ice bath, and stir overnight at room temperature. TLC (pet...

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Abstract

The invention relates to a synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1, 4-oxyaza-4, 5-dicarboxylic acid, and solves the technical problems of difficult synthesis operation and expensive raw materials in existing methods. The method includes: reacting 2-benzylaminoethanol as the starting raw material with t-butyloxycarboryl to protect amino to obtain tert-butylbenzyl(2-hydroxyethyl)carbamate, reacting the product with sodium hydride in ice bath, then reacting the reaction product with ethyl bromoacetate to obtain ethyl 2-(2-(benzyl)t-butyloxycarboryl)amine)ethoxy)acetic acid, then removing Boc with a hydrochloric acid ethyl acetate solution to obtain ethyl 2-(2-(benzylamine)ethoxy)acetic acid hydrochloride, and then in the presence of alkali, reacting the ethyl 2-(2-(benzylamine)ethoxy)acetic acid hydrochloride with ethyl bromoacetate to obtain ethyl 2-(benzyl(2-(2-ethoxy-2-oxoethoxy)ethyl)amino)acetic acid, using palladium hydroxide as the catalyst, in the presence of di-tert-butyl carbonate, removing Boc from benzyl with hydrogen to obtain ethyl 2-((t-butyloxycarboryl)(2-(2-ethoxy-2-oxoethoxy)ethyl)amino)acetic acid, and finally under a potassium tert-butoxide alkaline condition and with toluene as the solvent, conducting backflow and ring closing so as to obtain a final compound.

Description

technical field [0001] The invention relates to a practical synthesis method of 4-tert-butyl-5-ethyl-6-oxo-1,4-oxazepine-4,5-dicarboxylic acid. Background technique [0002] 4-tert-butyl-5-ethyl-6-oxo-1,4-oxazepine-4,5-dicarboxylic acid (CAS No.: 1330763-23-9) is a useful intermediate in organic synthesis , the market sales are better. However, there is a lack of reports on its industrial synthesis methods in the literature, and various derivatives with this compound as the core have important roles in organic synthesis and drug synthesis. Contents of the invention [0003] The purpose of the present invention is to develop a kind of 4-tert-butyl-5-ethyl-6-oxo-1,4-oxazepine-4 with easy to get raw material, easy to operate, easy to control reaction and high yield. , The synthesis method of 5-dicarboxylic acid mainly solves the technical problem that there is no suitable industrial synthesis method at present. [0004] Technical solution of the present invention: a synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/10
CPCY02P20/55
Inventor 徐学芹周强刘月领安自强刘璇何燕平于华夏章洋毛延军于凌波何振民马汝建陈民章傅小勇王文贵
Owner CHANGZHOU HEQUAN PHARMA CO LTD
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