Preparation method of 1-phenylmethyl-5-(tert-butyloxycarbonyl) octahydropyrrolopyrrole-2-carboxylic acid

A technology of tert-butoxycarbonyl and octahydropyrrole, which is applied in the fields of organic chemical methods, organic chemistry, bulk chemical production, etc., can solve the problems of no suitable industrial synthesis methods, and achieve reasonable reaction process design, high yield, and easy operation convenient effect

Active Publication Date: 2020-09-04
WUXI APPTEC
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Preparation method of 1-phenylmethyl-5-(tert-butyloxycarbonyl) octahydropyrrolopyrrole-2-carboxylic acid

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[0012] The first step: Compound 1 (259 g 1.11 mol), benzylglycine ethyl ester (251 g, 1.3 mol) and triethylamine (168 g, 1.7 mol) were dissolved in toluene (3.0 L), and the Water was removed from the water tank and refluxed at 110-130° C. for 12 hours. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1) showed that the raw material was completely consumed. The mixture was washed with 1N HCl (600 mL x 2) and brine (600 mL), dried over anhydrous sodium sulfate, and concentrated to give compound 2 (380 g, yield: 100%) as an orange oil.

[0013] The second and third steps: Compound 2 (101 g 0.25 mol) was dissolved in glacial acetic acid (100 mL), and acetic acid hydrobromic acid (200 mL) was added dropwise at 0°C. The mixture was stirred at room temperature 25°C for 2 hours. TLC (petroleum ether / ethyl acetate = 4 / 1) indicated complete consumption of starting material. The reaction solution was concentrated to dryness, and the pH was adjusted to 8-9 with aqueous sodium carbonate...

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Abstract

The invention relates to a preparation method of 1-phenylmethyl-5-(tert-butyloxycarbonyl) octahydropyrrolopyrrole-2-carboxylic acid, and mainly solves the technical problem that no suitable industrialsynthesis method exists at present. The method comprises the following four steps: 1, adding triethylamine into anhydrous toluene to obtain a compound 2 from a compound 1 and ethyl phenylmethylglycinate; 2, dissolving the compound 2 in glacial acetic acid under the action of hydrobromic acid acetate to obtain a compound 3; 3, dissolving the compound 3 in methanol, and adding Boc anhydride to obtain a compound 4; and 4, dissolving the compound 4 in water and methanol, adding sodium hydroxide, and hydrolyzing to obtain a compound 5, wherein the reaction formula is shown in the specification.

Description

technical field [0001] The present invention relates to the synthetic method of compound (2S, 3aS, 6aS)-1-benzyl-5-(tert-butoxycarbonyl) octahydropyrrolo[3,4-b]pyrrole-2-carboxylic acid, referred to as 1- Benzyl-5-(tert-butoxycarbonyl) octahydropyrrolopyrrole-2-carboxylic acid preparation method. Background technique [0002] The compound (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrolo[3,4-b]pyrrole-2-carboxylic acid (CAS: 1210431-08-5) and Related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, there are few reports on the synthesis of (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrolo[3,4-b]pyrrole-2-carboxylic acid. Currently, there are few reports on the synthesis of (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrolo[3,4-b]pyrrole-2-carboxylic acid. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitabl...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04C07B2200/07Y02P20/55
Inventor 张大为周强高明飞姚宝元兰倩倩赵廷王曦卫维魏昕睿谭汝鹏贾涛白有银孙春付新雨于凌波马汝建
Owner WUXI APPTEC
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