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Preparation method of racemic homocitric acid lactone

A citric acid, racemic technology, applied in the direction of organic chemistry and the like, can solve problems such as unsuitable scale preparation, and achieve the effects of high reaction yield, good application prospect and simple preparation process

Inactive Publication Date: 2007-03-14
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route has certain practical value, but it is not suitable for large-scale preparation

Method used

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  • Preparation method of racemic homocitric acid lactone
  • Preparation method of racemic homocitric acid lactone

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Synthesis of triethyl homocitrate 2a: Add n-BuLi (2.5M solution in n-hexane, 1.42mmol, 0.57ml) to a solution of HMDS (0.35ml, 1.65mmol) in THF (1ml) under ice-cooling, After reacting for 30min, cool to -78°C, add ethyl acetate (0.37ml, 1.42mmol), react for 30min, add a solution of 1a (238mg, 1.18mmol) in THF (3.5ml), react for 3h, add saturated NH 4 Quenched with Cl, extracted with ether, combined the organic phases, washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, flash column chromatography (ethyl acetate:petroleum ether=1:6~1:4) gave compound 2a with a yield of 73%. IR(film)ν max : 3505, 2982, 2938, 1736, 1446, 1373, 1191cm -1 ; 1 HNMR (400MHz, CDCl 3 )δ: 2.68(d, J=16.2Hz, 1H), 2.94(d, J=16.2Hz, 1H), 1.31(t, J=7.1Hz, 3H), 1.25(t, J=7.1Hz, 3H) , 1.25(t, J=7.1Hz, 3H), 3.77(s, 1H-OH), 4.13(qq, overlapped, J=7.1Hz, 4H), 4.22~4.31(m, 2H), 2.02~2.07(m , 2H), 2.21~2.29(m, 1H), 2.46~2.54(m,...

Embodiment 2

[0025] Compound 2a was prepared from compound 1a according to the method of Example 1.

[0026] Compound 3 was prepared from compound 2a according to the method of Example 1, using trifluoroacetic acid instead of formic acid, and the rest of the operations were the same, with a yield of 91%.

Embodiment 3

[0028] Compound 2a was prepared from compound 1a according to the method of Example 1, and the molar ratio of base and ester was 1:2.

[0029] Compound 3 was prepared from compound 2a according to the method of Example 1, trifluoroacetic acid was added to formic acid, the ratio of formic acid to trifluoroacetic acid was 1:1, the molar ratio of compound 2a and acid was 1:10, and the rest of the operations were the same.

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Abstract

The present invention relates to homocitric lactone, and is especially the simple large scale process of preparing racemic homocitric lactone with facile cheap 2-keto glutaric ester as material. The preparation process includes the reaction of 2-keto glutaric ester with negative ion in solvent, extraction, concentration and chromatographic column purification to form one intermediate compound; and the refluxing of the intermediate compound in formic acid, acetic acid and / or trifluoroacetic acid to obtain homocitric lactone. The negative ion is formed with one kind of ester selected from ethyl acetate, methyl acetate and tert-butyl acetate, and one kind of alkali selected from hexamethyl disilicoamido lithium formed with n-butyl lithium and hexamethyl disilane and diisopropylamino lithium formed with n-butyl lithium and diisopropylamine.

Description

technical field [0001] The invention relates to a homocitrate lactone, in particular to a method for preparing racemic homocitrate lactone in a simple and large-scale manner by using 2-oxoglutarate as a raw material. Background technique [0002] Homocitric acid (Homocitric acid) is an important biochemical reagent, it is an important intermediate in the biosynthesis of lysine in fungi and euglena, and it is considered as a potential antibacterial drug. At the same time, homocitric acid plays a very important role in the process of nitrogenase catalyzing the reduction of nitrogen to ammonia. At present, the amount of homocitric acid synthesized by enzymatic method is generally within a few hundred milligrams, which makes the price of homocitric acid very expensive (≥$1000 / g), and only one company in the world sells it, which greatly limits related research . Therefore, it is particularly important to develop a simple and scalable method for the preparation of homocitric ac...

Claims

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Application Information

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IPC IPC(8): C07D307/33
Inventor 黄培强陈玲艳张洪奎
Owner XIAMEN UNIV
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