Process for synthesizing 7-chloro-2-oxo-heptanoic acid

A synthesis method and technology of ethyl oxoheptanoate, applied in the field of synthesis of 7-chloro-2-oxoheptanoic acid, can solve the problems of high cost, long steps, difficult raw materials and the like, and achieve low cost and reaction conditions. Gentle, simple-to-process effect

Inactive Publication Date: 2005-03-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route needs to be synthesized in four steps, the steps are long, the raw materials are not easy to obtain, and the cost is high

Method used

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  • Process for synthesizing 7-chloro-2-oxo-heptanoic acid
  • Process for synthesizing 7-chloro-2-oxo-heptanoic acid
  • Process for synthesizing 7-chloro-2-oxo-heptanoic acid

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Embodiment 1

[0015] Embodiment 1: A kind of synthetic method of 7-chloro-2-oxoheptanoic acid, using 1-bromo-5-chloro-pentane as the main starting material, is prepared through the following steps in sequence:

[0016] Step (1), first manufacture the single Grignard reagent of 1-bromo-5-chloro-pentane according to the conventional steps of Grignard reagent. Add 2.40 g (0.1 mol) of magnesium into the reactor, then add 10 ml of anhydrous ether and 0.2 ml of bromoethane, and stir to initiate the reaction. 18.6g (0.1mol) of 1-bromo-5-chloropentane was mixed with 70ml of anhydrous ether and then slowly added dropwise, the rate of addition was based on the slow reflux of ether. After dropping, heat the reaction until the magnesium powder is completely dissolved. The prepared single Grignard reagent is sealed and cooled for later use. Then carry out the addition reaction. Add 13.1 g (0.09 mol) of diethyl oxalate and 30 ml of anhydrous ether into a dry reaction flask, stir mechanically, protect ...

Embodiment 2

[0018] Embodiment two: a kind of synthetic method of 7-chloro-2-oxoheptanoic acid, take 1-bromo-5-chloro-pentane as main starting material, make through following steps successively:

[0019] Step (1), first manufacture the single Grignard reagent of 1-bromo-5-chloro-pentane according to the conventional steps of Grignard reagent. Add 2.88 g (0.12 mol) of magnesium into the reaction flask, then add 10 ml of anhydrous ether and 0.2 ml of ethyl bromide, and stir to initiate the reaction. 18.6g (0.1mol) of 1-bromo-5-chloropentane was mixed with 70ml of anhydrous ether and then slowly added dropwise, the rate of addition was based on the slow reflux of ether. After dropping, heat the reaction until the magnesium powder dissolves. The Grignard reagent is sealed and cooled for later use. Then carry out the addition reaction. Add 14.6 g (0.1 mol) of diethyl oxalate and 30 ml of anhydrous ether into a dry reaction flask, stir mechanically, protect with nitrogen, cool down to -15°C,...

Embodiment 3

[0021] Embodiment three: a kind of synthetic method of 7-chloro-2-oxoheptanoic acid, take 1-bromo-5-chloro-pentane as main starting material, make through following steps successively:

[0022] Step (1), first manufacture the single Grignard reagent of 1-bromo-5-chloro-pentane according to the conventional steps of Grignard reagent. Add 3.12 g (0.13 mol) of magnesium into the reaction flask, then add 10 ml of anhydrous ether and 0.2 ml of ethyl bromide, and stir to initiate the reaction. 18.6g (0.1mol) of 1-bromo-5-chloropentane was mixed with 70ml of anhydrous ether and then slowly added dropwise, the rate of addition was based on the slow reflux of ether. After dropping, heat the reaction until the magnesium powder dissolves. The Grignard reagent is sealed and cooled for later use. Then carry out the addition reaction. Add 16.1 g (0.11 mol) of diethyl oxalate and 30 ml of anhydrous ether into a dry reaction flask, stir mechanically, protect with nitrogen, cool down to -60...

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Abstract

The process of synthesizing 7-chloro-2-oxo-heptanoic acid includes preparing 1-bromo-5-chloro-pentane into Dangler reagent, addition reaction of the Dangler reagent with diethyl oxalate, and hydrolysis to obtain 7-chloro-2-oxo-heptanoic acid. The present invention has simple technological process, mild reaction condition, low cost and total yield up to 43.0 %.

Description

technical field [0001] The invention relates to a synthesis method of 7-chloro-2-oxoheptanoic acid. Background technique [0002] [0003] The 7-chloro-2-oxoheptanoic acid with molecular formula as shown in 1 can be used as an intermediate in the synthesis of cilastatin (a renal dehydrodipeptidase inhibitor) to replace the 7-bromodipeptidase used in the prior art -2-oxoheptanoic acid (molecular formula 2). The existing technology of synthesizing 7-bromo-2-oxoheptanoic acid is as follows: [0004] Graham et al. (J.Med Chem.1987,30,1074) reacted 2,2-diethoxy ethyl acetate with 1,3-propanedithiol to obtain 1,3-dithiane-2-carboxylic acid ethyl The ester is reacted with 1,5-dibromopentane in the presence of sodium hydrogen, then oxidized and hydrolyzed to obtain 7-bromo-2-oxoheptanoic acid with a total yield of 49%. This route will be synthesized through four steps, the steps are longer, the raw materials are not easy to get, and the cost is higher. Contents of the invent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/21
Inventor 陈新志石晓华金放鸣李成明
Owner ZHEJIANG UNIV
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