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Method for synthesizing diketo nitrogen-containing compound and intermediates thereof

A synthetic method, methyl technology, applied in the field of synthesis of nitrogen-containing diketone compounds with five-membered rings and six-membered rings, which can solve the problems of affecting the reaction yield, difficult to dry out, cumbersome operation, etc., and achieves high yield and easy operation , low-cost effect

Inactive Publication Date: 2012-07-04
CHONGQING HUAPONT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The method of prior art has two problems: the one, it is difficult to monitor the progress of reaction, can not understand the progress situation of reaction in the reaction, can not more accurately know whether the reaction is complete
We found that the reaction process cannot be well monitored by TLC or HPLC, and the color development with ninhydrin is not only troublesome but also difficult to distinguish, resulting in unstable yield and poor operability
Another problem is that in the process of synthesizing the salt of the intermediate amino acid ester in the first step, it is very easy to absorb water, which causes the salt part of the amino acid ester to absorb water and become thinner when filtering, which greatly affects the yield of the reaction and is difficult to drain. , cumbersome operation

Method used

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  • Method for synthesizing diketo nitrogen-containing compound and intermediates thereof
  • Method for synthesizing diketo nitrogen-containing compound and intermediates thereof
  • Method for synthesizing diketo nitrogen-containing compound and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 2, the preparation of 4-piperidine diketone

[0037] 1. Preparation of β-alanine benzyl ester p-toluenesulfonate:

[0038] Add 200g of β-alanine, 465g of p-toluenesulfonic acid, 970g of benzyl alcohol and 4L of toluene in sequence into a 10L three-necked reaction flask, stir, the reaction solution becomes turbid, heated in an oil bath, dissolves, and the reaction solution becomes a clear and transparent colorless solution; Heat to reflux to separate water, judge the end point of the reaction with TLC (developing agent CHCl 3 :CH 3 OH=5:2 Rf=0.56). Add 1200ml of toluene and leave it overnight at room temperature (16°C). A large number of flaky crystals were precipitated, and the filter cake was fully washed by filtering 3×500 ml of petroleum ether, and dried under reduced pressure at 80° C. to obtain 773 g of flaky white crystals, with a yield of 98.0%. HPLC analysis 99.16%

[0039] 2. Preparation of N-(3-ethoxy-1,3-dioxypropyl)-beta-alanine benzyl este...

Embodiment 2

[0047] Example 2 Preparation of 2,4-tetrahydropyrrole diketone

[0048] 1. Preparation of glycine p-methylbenzyl benzenesulfonate

[0049] Add 150g of glycine, 344g of benzenesulfonic acid, 860g of p-methylbenzyl alcohol and 3.5L of toluene into a 5L three-necked reaction flask in sequence, stir, the reaction solution becomes turbid, heated in an oil bath, dissolves, and the reaction solution becomes a clear and transparent colorless solution; Heat to reflux to separate water, judge the end point of the reaction with TLC (developing agent CHCl 3 :CH 3 OH=5:2 Rf=0.55). Add 1100ml of toluene and leave it overnight at room temperature (16°C). A large number of crystals were precipitated, and the filter cake was fully washed by filtering 3×500ml of petroleum ether, and dried under reduced pressure at 80°C to obtain 665g of flaky white crystals, the yield was 98.7%, and the HPLC analysis was 99.42%

[0050] 2. Preparation of N-(3-methoxy-1,3-dioxypropyl)-glycine p-methylbenzyl ...

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Abstract

The invention relates to a method for synthesizing a diketo nitrogen-containing compound. In the method, an alpha or beta amino acid is esterified by an aromatic alcohol having an ultraviolet absorbing group, the resulting product undergoes condensation with a propane diacid monoester, and the diketo nitrogen-containing compound is obtained by cyclization. The method has the advantages that: two reaction intermediates are new compounds; the reaction process can be monitored during operation; and water absorption is not easy to occur. Therefore, the final product yield of the method is high and stable.

Description

Technical field: [0001] The invention relates to a method for synthesizing a diketo nitrogen-containing ring. It specifically relates to a synthesis method of five-membered ring and six-membered ring nitrogen-containing diketone compound. The present invention also relates to two novel compounds that are intermediates of the synthesis process. Background technique: [0002] THE JOURNAL OF ANTIBIOTICS 1980, 33 (2), 173-181 reported the synthesis method of five-membered ring and six-membered ring nitrogen-containing diketone compound, USP5196534 reported the synthesis method of six-membered ring nitrogen-containing diketone compound, the two methods are the same, Both use amino acid and alkyl alcohol to reflux under the catalyst of inorganic acid to generate amino acid ester salt, condense with malonic acid monoester to obtain amide compound, and then obtain cyclic compound through the action of sodium alkoxide, and finally obtain five-membered ring through decarboxylation A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D227/08C07D207/36C07D211/86
Inventor 郝光富刘汉光邹长忠
Owner CHONGQING HUAPONT PHARMA
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