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Synthetic method of 2-(4-tertbutyloxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid

A technology of tert-butoxycarbonyl and synthetic method, applied in the synthesis field of 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid, can solve the problem that no effective synthetic method has been found, etc. problem, to achieve the effect of cheap reagents and simple reaction conditions

Inactive Publication Date: 2017-09-15
GL BIOCHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a synthetic method of 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid, mainly to solve the technical problem that there is no effective synthetic method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] step 1:

[0010] Add methyl 1-naphthaleneacetate (21.0 g, 105 mmol), carbon tetrachloride (200 mL), N-bromosuccinimide (20.6 g, 115.5 mmol) and benzoyl peroxide into a three-necked flask (2.5 g, 10.5 mmol). The reaction solution was stirred at 80°C for 2 hours. The reaction solution was cooled to room temperature, filtered to remove the solid, and the filtrate was spin-dried; the residue was dissolved in ethyl acetate (200 mL), and successively washed with 10% citric acid aqueous solution (50 mL) and saturated sodium bicarbonate aqueous solution (50 mL ) and saturated saline (50 mL); dried over sodium sulfate and filtered. The filtrate was spin-dried to obtain a brown liquid, compound 1 (26.0 g, 93.2 mmol, 89%). 1 H NMR (400 MHz, CDCl 3 ): 8.10 (m, 1H), 7.87 (m, 2H), 7.77 (m, 1H), 7.56(m, 1H), 7.53 (m, 1H), 7.46 (m, 1H), 6.17 (s, 1H) , (s, 3H) ppm. LC-MS (ESI): m / z 279.32 [M+H] + ;

[0011] Step 2:

[0012] Add compound 1 (26.0 g, 93.2 mmol), N,N-dimethylformami...

Embodiment 2

[0015] Example 2, step 1: methyl 1-naphthalene acetate neutralizes N-bromosuccinimide in carbon tetrachloride, the reaction time of benzoyl peroxide is 1 hour, and the reaction temperature is 90°C; the rest are implemented in the same way example 1.

Embodiment 3

[0016] Example 3, step 1: methyl 1-naphthalene acetate neutralizes N-bromosuccinimide in carbon tetrachloride, the reaction time of benzoyl peroxide is 3 hours, and the reaction temperature is 70°C; the rest are implemented in the same way example 1.

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PUM

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Abstract

The invention relates to a synthetic method of 2-(4-tertbutyloxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid. The method mainly solves the technical problems of existing ineffective synthetic methods. The synthetic method in the invention comprises the following steps: brominating methyl 1-naphthaleneacetate to generate a compound 1; nucleophilically substituting bromine to generate a compound 2; and hydrolyzing carboxylate under the action of lithium hydroxide to generate carboxylic acid and the target compound 3, wherein a reaction equation is shown in the description. The synthetic method has the advantages of simple reaction principle in the whole synthesis process, cheap raw materials, and easiness in purification.

Description

technical field [0001] The present invention relates to the synthesis of 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid (CAS: 885274-72-6). Background technique [0002] 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid is widely used as a pharmaceutical intermediate. But so far there is no public report about its industrial synthesis method. Contents of the invention [0003] The purpose of the present invention is to provide a synthetic method of 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid, which mainly solves the technical problem that there is no effective synthetic method. [0004] The technical scheme of the present invention is: a kind of synthetic method of 2-(4-tert-butoxycarbonyl-piperazinyl)-2-(1-naphthyl)acetic acid, it is characterized in that comprising the following steps: the first step, after Under the catalysis of benzoyl oxide, methyl 1-naphthylacetate reacts with N-bromosuccinimide in carbon tetrachlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/215
CPCC07D295/215
Inventor 徐红岩马敬祥
Owner GL BIOCHEM SHANGHAI