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A kind of synthetic method of α-amino-γ-carbonylpimelate compound

A technology of carbonylpimelic acid ester and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, and preparation of cyanide reactions, etc., and can solve problems such as difficult synthesis or acquisition of reaction substrates, negative environmental impacts, and increased costs , to achieve the effects of fast reaction rate, less environmental pollution and mild synthesis conditions

Active Publication Date: 2020-11-24
NORTHWEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above technique of synthesizing oxopimelate, some methods have used precious metal catalysts, which are difficult to synthesize or obtain reaction substrates by simple methods; or use some solvents that are difficult to handle after the reaction, which not only increases the cost of synthesis, but also Refractory metal catalysts have a large negative impact on the environment
These shortcomings have greatly hindered the application of the above synthetic methods to industrial production.

Method used

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  • A kind of synthetic method of α-amino-γ-carbonylpimelate compound
  • A kind of synthetic method of α-amino-γ-carbonylpimelate compound
  • A kind of synthetic method of α-amino-γ-carbonylpimelate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 7-benzyl 1-methyl-4-oxo-2-(p-tolylamino)pimelate

[0026]

[0027] In a 25 ml round-bottomed flask, add magnetons, add 2-(p-tolylamino)methyl acetate (0.3 mmol), acetonitrile (6 ml), CuCl 2 (20 mol%), H 2 SO 4 (30 mol %) , stirred at room temperature for 2 hours, washed and extracted, separated by column chromatography; then added BnBr (3.2eq), K 2 CO 3 (2.4eq), DMF, reacted for 1 hour, washed to remove DMF, and separated by column chromatography (silica gel: 200~300 mesh, eluent volume ratio: petroleum ether: acetone = 3:1), to obtain a light yellow oily liquid The pure product is 7-benzyl 1-methyl-4-oxo-2-(p-tolylamino)pimelate. The yield was 50%.

[0028] The NMR data of this compound are as follows: 1 H NMR (600 MHz, CDCl 3 ) δ 7.37 – 7.34 (m, 2H),7.33 (d, J = 2.2 Hz, 2H), 7.32 (d, J = 3.1 Hz, 1H), 6.98 (d, J = 8.1 Hz, 2H),6.56 (d , J = 8.4 Hz, 2H), 5.10 (s, 2H), 4.42 (d, J = 5.3 Hz, 1H), 4.23 (s,1H), 3.70 (s, 3H), 3.00 (d, J = 5.5...

Embodiment 2

[0029] Embodiment 2: the synthesis of 4-oxo-2-((4-phenoxyphenyl) amino) dimethyl pimelate

[0030]

[0031]In a 25 ml round-bottomed flask, add magnetons, add 2-((4-phenoxyphenyl)amino)methyl acetate (0.3 mmol), acetonitrile (6 ml), CuCl 2 (20 mol%), H 2 SO 4 (30 mol %) , stirred at room temperature for 2 hours, washed and extracted, separated by column chromatography; then added CH 3 I (3.2eq), K 2 CO 3 (2.4eq), DMF, reacted for 1 hour, washed to remove DMF, and separated by column chromatography (silica gel: 200~300 mesh, eluent volume ratio: petroleum ether: acetone = 3:1), to obtain a light yellow oily liquid The pure product is dimethyl 4-oxo-2-((4-phenoxyphenyl)amino)pimelate. The yield was 81%.

[0032] The NMR data of this compound are as follows: 1H NMR (600 MHz, CDCl3) δ 7.28 – 7.25 (m, 2H),7.00 (t, J = 7.4 Hz, 1H), 6.91 (dd, J = 8.6, 0.9 Hz, 2H), 6.89 (d, J = 8.8Hz, 2H), 6.65 (d, J = 8.9 Hz, 2H), 4.42 (d, J = 6.7 Hz, 1H), 4.32 (s, 1H), 3.74 (s, 3H), 3.66 ...

Embodiment example 3

[0033] Example 3: Synthesis of dimethyl 2-((4-iodophenyl)amino)-4-oxopimelate

[0034]

[0035] The synthetic route and separation method are the same as in Example 2, wherein only the raw material 2-((4-phenoxyphenyl)amino)methyl acetate is replaced with 2-(4-iodophenylamino)methyl acetate. The pure product, dimethyl 2-((4-iodophenyl)amino)-4-oxopimelate, was obtained as light yellow oily liquid. The yield was 80%.

[0036] The NMR data of this compound are as follows: 1 H NMR (600 MHz, CDCl 3 ) δ 7.43 – 7.40 (m, 2H),6.42 (d, J = 8.7 Hz, 2H), 4.46 (d, J = 8.7 Hz, 1H), 4.41 – 4.37 (m, 1H), 3.72(s, 3H) , 3.65 (s, 3H), 3.01 (dd, J = 5.0, 3.1 Hz, 2H), 2.74 – 2.70 (m, 2H),2.59 (t, J = 6.5 Hz, 2H). 13 C NMR (151 MHz, CDCl 3 ) δ 206.1, 172.9, 172.8, 146.0, 137.9, 115.8, 79.5, 52.6, 52.4, 51.7, 44.5, 37.6, 27.6.

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Abstract

The invention provides a method for synthesizing alpha-amino-gamma-carbonyl pimelic ester compounds. The method comprises the following steps: taking alpha-angelica lactone and an N-aryl glycine derivative as raw materials, taking cheap metal salt as a catalyst and protonic acid as an additive in an organic solvent, and performing normal temperature in air to form the pimelic ester compounds. Themethod is low in prices of reaction reagents, simple in reaction steps, easy to operate, low in production cost and small in environment pollution; the reaction time is short, aftertreatment is simpleand convenient, the yield is high, the purity is good, and the method is applicable to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing carbonylpimelate compounds, in particular to a method for synthesizing α-amino-γ-carbonylpimelate compounds, and belongs to the technical field of chemical synthesis. Background technique [0002] Carbonylpimelate plays an important role in the synthesis of some branched macromolecules or macrocyclic compounds that are difficult to synthesize by simple methods. The synthesis of branched macromolecules can be used as a multi-directional synthetic starting point. All natural compounds with biological activity contain polycarbonyl structures. Polycarbonyl compounds are not only important precursors for the synthesis of non-natural compounds, but also important precursors for the synthesis of many natural compounds. Due to various difficulties in synthesizing polycarbonyl compounds, there are not many types of polycarbonyl compounds in the current chemical field. [0003] The structural formula of α-amino...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/16C07C229/24
CPCC07C227/16C07C229/24
Inventor 霍聪德吴睿
Owner NORTHWEST NORMAL UNIVERSITY
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