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Preparation method of ethyl 7-chloro-2-oxoheptanoate

A technology of ethyl oxoheptanoate and diethyl oxalate, which is applied in the field of preparation of ethyl 7-chloro-2-oxoheptanoate by the Grignard method, to achieve the effect of reducing production cost and improving quality

Active Publication Date: 2014-04-09
河北慧林生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, it is difficult to prepare Grignard reagents in benzene solvents, especially toluene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The first step: preparation of Grignard reaction solution

[0045] Add 5 kg of magnesium metal and 140 kg of anhydrous ether into a dry and nitrogen-filled reactor; mix 100 kg of 1-bromo-5-chloropentane and 176 kg of anhydrous toluene and add to In the dropping funnel, slowly drop into the above reaction kettle; after the reaction is initiated, the temperature is lowered and the reaction is continued dropwise. At the same time, 8.2 kg of magnesium metal strips are added to it in three times. The reaction temperature is controlled at -15°C and the magnesium metal It should be completely added 30 minutes before the addition of the mixed liquid to ensure sufficient reaction time; the Grignard reaction liquid is obtained after the reaction is completed, and it is sealed and frozen for later use;

[0046] The second step condensation reaction

[0047] Add 80 kilograms of diethyl oxalate and 176 kilograms of anhydrous toluene into the second reactor under nitrogen protection...

Embodiment 2

[0051] The first step: preparation of Grignard reaction solution

[0052] Add 5 kg of magnesium metal and 145 kg of anhydrous ether into a dry and nitrogen-filled reactor and stir; mix 100 kg of 1-bromo-5-chloropentane and 180 kg of anhydrous toluene and add to In the dropping funnel, slowly drop into the above reaction kettle; after the reaction is initiated, the temperature is lowered and the reaction is continued dropwise. At the same time, 8.1 kilograms of magnesium metal strips are added to it in four times. The reaction temperature is controlled at 0°C and the magnesium metal It should be completely added 40 minutes before the addition of the mixed liquid to ensure sufficient reaction time; the Grignard reaction liquid is obtained after the reaction is completed, and it is sealed and frozen for later use;

[0053] The second step condensation reaction

[0054] Add 80 kilograms of diethyl oxalate and 180 kilograms of anhydrous toluene into the second reactor under nitr...

Embodiment 3

[0058] The first step: preparation of Grignard reaction solution

[0059] Add 5 kg of magnesium metal and 130 kg of anhydrous ether into a dry and nitrogen-filled reactor and stir; mix 100 kg of 1-bromo-5-chloropentane and 165 kg of anhydrous toluene and add to In the dropping funnel, slowly drop into the above reaction kettle; after the reaction is initiated, the temperature is lowered and the reaction is continued dropwise. At the same time, 8.0 kg of magnesium metal bars are added to it in five times. The reaction temperature is controlled at -10°C and the metal Magnesium should be completely added 45 minutes before the addition of the mixed liquid to ensure sufficient reaction time; the Grignard reaction liquid should be obtained after the reaction is completed, and it should be sealed and frozen for later use;

[0060] The second step condensation reaction

[0061] Add 80 kilograms of diethyl oxalate and 165 kilograms of anhydrous toluene into the second reactor under ...

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Abstract

The invention belongs to the technical field of preparation of pharmaceutical intermediates and discloses a preparation method of ethyl 7-chloro-2-oxoheptanoate. The preparation method comprises the preparation steps of performing Grignard reaction on 1-bromo-5-chloropentane and magnesium to obtain a Grignard reagent reaction solution; performing condensation reaction on the reaction solution and diethyl oxalate, and performing treatment to obtain a crude product of ethyl 7-chloro-2-oxoheptanoate; performing condensation reaction and hydrolysis reaction on the crude product and a purifying agent of a hydrazine compound, and rectifying to obtain ethyl 7-chloro-2-oxoheptanoate. The method for preparing ethyl 7-chloro-2-oxoheptanoate has the characteristics of relatively high product yield, low production cost and little pollution in preparation process.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, in particular to a preparation method for synthesizing ethyl 7-chloro-2-oxoheptanoate by a Grignard method. Background technique [0002] Cilsatatin (cilsatatin), the chemical name is (+)-(Z)-7-[(2R)-(2-amino-2-carboxyethyl)sulfur]-2-[(1S)-(2, 2-Dimethylcyclopropanecarboxamido)-2-heptenoic acid is a renal dehydrodipeptidase inhibitor developed by Merck in the United States, which can inhibit the broad-spectrum antimicrobial drug imine currently in clinical use. The renal metabolism of imipenem can increase the blood inhibitory concentration of imipenem while reducing renal toxicity, and the curative effect is very significant. Therefore, the compound preparation of cilastatin and imipenem can be used as a broad-spectrum antibacterial Drugs are increasingly used clinically. [0003] Imipenem is a thiamycin antibacterial drug with a carbapenem ring. Its antiba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/716C07C67/60C07C67/343
CPCC07C67/343C07C67/60C07C69/716
Inventor 孙德春
Owner 河北慧林生物科技有限公司
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