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1-Benzyl-5-(tert-butoxycarbonyl)octahydropyrrolopyrrole-2-carboxylic acid preparation method

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

Active Publication Date: 2022-05-17
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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  • 1-Benzyl-5-(tert-butoxycarbonyl)octahydropyrrolopyrrole-2-carboxylic acid preparation method

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Embodiment

[0012] Step 1: Compound 1 (259 g 1.11 mol), ethyl benzylglycinate (251 g, 1.3 mol) and triethylamine (168 g, 1.7 mol) are dissolved in toluene (3.0 L), removed with a water separator, reflux at 110-130 °C for 12 hours, TLC (petroleum ether / ethyl acetate volume ratio = 5 / 1) shows that the raw material is completely consumed. Wash the mixture with 1 N HCl (600 mL x 2) and brine (600 mL), dry with anhydrous sodium sulfate, and concentrate to give orange oily compound 2 (380 g, yield: 100%).

[0013] Steps 2 and 3: Dissolve Compound 2 (101 g 0.25 mol) in glacial acetic acid (100 mL) and drop hydrobromic acid acetate (200 mL) at 0 °C. The mixture was stirred at room temperature at 25 ° C for 2 hours. TLC (Petroleum Ether / Ethyl Acetate = 4 / 1) indicates that the raw material is completely consumed. Concentrate the reaction solution to dryness and adjust the pH = 8-9 with an aqueous sodium carbonate solution. Then add methanol (200 ml), Boc anhydride (70 g, 0.4 mol). The resulting solut...

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Abstract

The invention relates to a method for preparing 1-benzyl-5-(tert-butoxycarbonyl) octahydropyrrolopyrrole-2-carboxylic acid, which mainly solves the technical problem that there is no suitable industrial synthesis method at present. The present invention is divided into four steps. In the first step, at first compound 2 is obtained by adding triethylamine into anhydrous toluene with compound 1 and benzylglycine ethyl ester. In the second step, compound 2 is dissolved in glacial acetic acid in acetic acid hydrobromic acid Compound 3 is obtained under the action of the third step. Compound 3 is dissolved in methanol, and then Boc anhydride is added to obtain compound 4. In the fourth step, compound 4 is dissolved in water and methanol, and sodium hydroxide is added to be hydrolyzed into compound 5. The reaction formula is as follows: .

Description

Technical field [0001] The present invention relates to a synthesis method of compounds (2S,3aS,6aS)-1-benzyl-5- (tert-butoxycarbonyl) octahydropyrrololulo [3,4-b] pyrrole-2-carboxylic acid, abbreviated as 1-benzyl-5- (tert-butoxycarboxyl) octahydropyrrolopryle-2-carboxylic acid preparation method. Background [0002] Compounds (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrole[3,4-b]pyrrole-2-carboxylic acid (CAS: 1210431-08-5) and related derivatives have been widely used in medicinal chemistry and organic synthesis. At present, the synthesis method of (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrole[3,4-b]pyrrole-2-carboxylic acid has rarely been reported in the literature. At present, the synthesis method of (2S,3aS,6aS)-1-benzyl-5-(tert-butoxycarbonyl)octahydropyrrole[3,4-b]pyrrole-2-carboxylic acid has rarely been reported in the literature. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operat...

Claims

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Application Information

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Patent Type & Authority Patents(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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