Method for preparing 3-(3-chloropropyl)-4-oxopyrrolidine-1-ethyl carboxylate

A technology of oxopyrrolidine and ethyl propionate, which is applied in the direction of organic chemistry, can solve the problems of high environmental hazards, complicated processes, and low safety, and achieve the effects of increased overall yield, safe reaction process, and simplified operation

Inactive Publication Date: 2018-11-23
江苏八巨药业有限公司
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  • Abstract
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Problems solved by technology

[0004] In order to solve the traditional 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylate synthesis method in the prior art, there are complex processes, great environmental hazards, low safety and low yield Problem, the present invention provides a new method for the preparation of ethyl 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylate

Method used

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  • Method for preparing 3-(3-chloropropyl)-4-oxopyrrolidine-1-ethyl carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1. At room temperature, add glycine ethyl ester (103.12g, 1mol), ethanol (458ml), and dropwise add ethyl acrylate (150g, 1.5mol) to the reactor, and the dropping time is controlled at about 5 hours (note that the temperature rise ), after dripping, keep it warm at 20±5°C for about 2 hours, and take a sample to control and detect that the reaction is complete. After the reaction, the system was transferred to a distillation reactor for distillation and concentrated to dryness at 45-50°C to obtain 197.3g of the product with a yield of 97.2%.

[0030] 2. At room temperature, add the previous step oil (197.3g, 0.972mol) to the reactor, add potassium iodide (4.32g, 26mmol), potassium carbonate (201.2g, 1.458mol), ethyl chloroformate (210.96g, 0.75mol), the temperature is 50±5°C, keep warm for 5 hours, filter with suction, rinse the filter cake with 100ml toluene, collect the filtrate, add sodium sulfate to the organic layer to dry, filter, rinse the filter cake with a small ...

Embodiment 2

[0035] 1. At room temperature, add glycine ethyl ester (103.12g, 1mol), ethanol (400ml), and dropwise add ethyl acrylate (105g, 1.05mol) to the reactor, and the dropping time is controlled at about 5 hours (note that the temperature rise ), after dripping, keep it warm at 20±5°C for about 2 hours, and take a sample to control and detect that the reaction is complete. After the reaction, the system was transferred to a distillation reactor for distillation and concentrated to dryness at 45-50°C to obtain 197.7g of the product with a yield of 97.4%.

[0036]2. At room temperature, add the previous step oil (197.7g, 0.974mol) to the reactor, add potassium iodide (2.71g, 16.3mmol), potassium carbonate (141.13g, 1.0227mol), ethyl chloroformate (158.5g , 1.461mol), the temperature is 50±5°C, keep warm for 5 hours, filter with suction, rinse the filter cake with 200ml of toluene, collect the filtrate, add sodium sulfate to the organic layer to dry, filter, rinse the filter cake with ...

Embodiment 3

[0041] 1. At room temperature, add glycine ethyl ester (103.12g, 1mol), ethanol (429ml), and dropwise add ethyl acrylate (130g, 1.3mol) to the reactor, and the dropping time is controlled at about 5 hours (note that the temperature rise ), after dripping, keep it warm at 20±5°C for about 2 hours, and take a sample to control and detect that the reaction is complete. After the reaction, the system was transferred to a distillation reactor for distillation and concentrated to dryness at 45-50°C to obtain 197.5g of the product with a yield of 97.3%

[0042] 2. At room temperature, add the previous step oil (197.5g, 0.973mol) to the reactor, add potassium iodide (1.4g, 21.2mmol), potassium carbonate (174.55g, 1.2649mol), ethyl chloroformate (184.74g , 1.70mol), the temperature is 50±5°C, keep warm for 5 hours, filter with suction, rinse the filter cake with 100ml of toluene, collect the filtrate, add sodium sulfate to the organic layer to dry, filter, rinse the filter cake with a ...

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Abstract

The invention provides a novel method for preparing 3-(3-chloropropyl)-4-oxopyrrolidine-1-ethyl carboxylate, aiming at solving the technical problems of a traditional 3-(3-chloropropyl)-4-oxopyrrolidine-1-ethyl carboxylate synthesis method in the prior art that a flow is complicated, the environmental hazards are great, the safety is low and the yield is low. The technology takes glycine ethyl ester and ethyl acrylate as starting raw materials, and steps of taking benzylamine as a raw material and carrying out debenzylation in a subsequent process are reduced; a process for preparing the 3-(3-chloropropyl)-4-oxopyrrolidine-1-ethyl carboxylate is greatly simplified; an existing technology needs 6-step reaction, and the technology only needs 5-step reaction, so that the operation is simplified and a production period is shortened; the method is applicable to large-scale industrial production. The technology does not take the benzylamine as the starting raw material, and the generation ofa cancer-causing high-hazard substance, i.e., benzyl chloride, is directly stopped from the source; harms to an ecological environment and body health of people are effectively avoided; a reaction process is safe and accords with environmental protection requirements of China better; the total yield is greatly improved and the yield is greater than or equal to 50 percent.

Description

technical field [0001] The invention discloses a method for preparing ethyl 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylate. Background technique [0002] Moxifloxacin hydrochloride belongs to the fourth generation of quinolones. It has strong antibacterial ability against Gram-negative bacteria and positive bacteria. It is effective against mycoplasma, chlamydia and Legionella. Effective against resistant bacteria. Since it was launched on the market, it has been obtained due to its broad antibacterial spectrum, strong antibacterial power, wide internal distribution, high drug concentration in the body, long half-life, good curative effect, small side effects, no cross-resistance with other antibacterial drugs, and almost no photosensitivity reaction. Widely used clinically. [0003] 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylic acid ethyl ester can be used as an intermediate for the synthesis of moxifloxacin hydrochloride, and in the prior art 3-(3-chloropropyl)-4- ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/24
CPCC07D207/24
Inventor 杨胜利王福军刘玉坤蒋荣彪张锦涛
Owner 江苏八巨药业有限公司
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