Carboxyl-containing polymer, preparation method and application thereof, as well as preparation method of supported catalyst and imipenem antibiotic intermediate

A polymer and supported technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, metal/metal oxide/metal hydroxide catalyst, etc., can solve heavy metal loss, production Problems such as high cost and poor mechanical properties can achieve the effect of reducing loss, improving mechanical properties and improving stability

Active Publication Date: 2015-01-07
ASYMCHEM LAB TIANJIN +4
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The present invention aims to provide a carboxyl-containing polymer, its preparation method and application, a supported catalyst and a preparation method of a penem antibiotic intermediate, so as to solve the loss of heavy metals caused by the poor mechanical properties of supported metal catalysts in the prior art , the problem of high production cost

Method used

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  • Carboxyl-containing polymer, preparation method and application thereof, as well as preparation method of supported catalyst and imipenem antibiotic intermediate
  • Carboxyl-containing polymer, preparation method and application thereof, as well as preparation method of supported catalyst and imipenem antibiotic intermediate
  • Carboxyl-containing polymer, preparation method and application thereof, as well as preparation method of supported catalyst and imipenem antibiotic intermediate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Synthetic monomer

[0090]

[0091] Add 4-vinylbenzyl alcohol (1,20 g, 149 mmol), dodecanedioic acid (2,30 g, 149 mmol) and 4-dimethylaminopyridine (1.82 g, 14.9 mmol) to tetrahydrofuran (300 mL) at room temperature Dicyclohexylcarbodiimide (32.1 g, 156 mmol) was added in portions to the solution. Stirring was continued at room temperature for 6 hours, and the insoluble matter was removed by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate (300 mL), washed with 1N hydrochloric acid (100 mL×2), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound 3 (22.4 g, 43% yield) and compound 4 (15.6 g, 45% yield).

[0092] Compound 3: 1 H NMR (CDCl 3 ,400MHz): δ1.24–1.36(m,12H),1.57–1.68(m,4H),2.31–2.38(m,4H),5.10(s,2H),5.26(d,J=10.9Hz,1H ), 5.75(d, J=17.6Hz, 1H), 6.71(dd, J=17.6, 10.9Hz, 1H), 7.31(d, J=8.1Hz, 2H), 7.40(d, J...

Embodiment 2

[0100] Synthetic monomer

[0101]

[0102] Add 4-vinylbenzyl chloride (7, 5.0 g, 31.92 mmol) in ethanol slowly to monomethylamine in ethanol (33.3%, 150 mL, 1.6 mol) at 40-45°C. After the reaction was complete, the reaction mixture was cooled, and potassium carbonate (6.62 g, 47.9 mmol) was added to continue stirring for 1 hour. Solid was removed by filtration, and the filtrate was concentrated to obtain the crude product of red oil compound 8 ( 1 H NMR yield: 52%), directly used in the next reaction.

[0103] Compound 8: 1 H NMR (CDCl 3 ,400MHz): δ2.45(s,3H),3.74(s,2H),5.22(d,J=10.9Hz,1H),5.73(d,J=17.6Hz,1H),6.71(dd,J= 17.6, 10.9Hz, 1H), 7.27(d, J=7.9Hz, 2H), 7.37(d, J=7.9Hz, 2H).

[0104] At room temperature, dodecanedioic acid (2, 20.6g, 89.5mmol) was dissolved in tetrahydrofuran (350mL), dicarbonyl imidazole (29.0g, 179mmol) was added in batches, stirring was continued for 1 hour, and then compound 8 (12.5 g, 1 H NMR content, 84.9 mmol). React at room temperatu...

Embodiment 3

[0113] Synthetic monomer

[0114]

[0115] Synthesis of Compound 13

[0116] At room temperature, 8-bromo-1-octanol (12, 11.0g, 52.6mmol), dihydropyran (22.1g, 263mmol) and pyridinium p-toluenesulfonate (528.7mg, 2.1mmol) were successively added to the reaction flask ) in dichloromethane (110 mL), stirred at room temperature until the reaction was complete. The reaction solution was concentrated until there was no fraction, and the crude product was purified by silica gel column chromatography to obtain compound 13 (14.1 g, 89% yield) as a yellow oil.

[0117] Compound 13: 1 H NMR (CDCl 3 ,400MHz): δ1.28–1.46(m,8H),1.48–1.62(m,6H),1.66–1.74(m,1H),1.79–1.87(m,3H),3.34–3.41(m,3H) ,3.46–3.51(m,1H),3.69–3.75(m,1H),3.83–3.88(m,1H),4.55–4.57(m,1H).

[0118] Synthesis of compound 16

[0119] Under ice-water bath, the DMF (2mL) solution of 4-vinylbenzyl alcohol (1,4.0g, 29.8mmol) was added in the DMF (36mL) suspension of NaH (60% content, 1.30g, 32.4mmol), and then in Stir fo...

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Abstract

The invention discloses a carboxyl-containing polymer, a preparation method and application thereof, as well as a preparation method of a supported catalyst and an imipenem antibiotic intermediate. The polymer is polymerized by three monomers with different structures. The carboxyl-containing polymer is a cross-linked polymer, contains a large number of benzene rings on a polymer chain, and can improve the rigidity and hardness of the polymer so as to effectively improve the mechanical properties of the polymer. Simultaneously, a carboxyl group is taken as a main functional group in the polymer and taken as a carrier, and a metal in the prepared supported metal catalyst has relatively good connection stability with the polymer through coordination reaction of the carboxyl group with the heavy metal. The stability of the supported metal catalyst can be improved through the factors in the two aspects, and the catalyst can be repeatedly used without losing catalytic activity. Simultaneously, the loss of active ingredients in the heavy metal can be reduced, and the production cost can be reduced.

Description

technical field [0001] The present invention relates to the field of chemical synthesis, in particular to a functionalized polymer containing carboxyl groups, its preparation method, its use in the preparation of supported metal catalysts, supported metal catalysts and supported metal catalysts to catalyze carbene insertion reactions A method for preparing an intermediate of penem antibiotics. Background technique [0002] Since Merrifield first reported the concept of light divinylbenzene-crosslinked chloromethylated polystyrene resins for solid-phase peptide synthesis almost half a century ago, polymers have been used in different ways for the synthesis and purification of compounds. become more and more common. Recently, various types of macromolecular materials such as JandaJel and Tentageld have been developed. They are not only used as supports for solid-phase synthesis, but also used for supporting reagents and catalysts. These materials have an advantage over Merr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F212/08C08F212/34C08F212/14C08F212/32C08F212/36C08F220/14C08F2/20B01J31/22C07D477/04C07D477/18
CPCC07D477/06C08F212/08C07D477/04C08F12/22C08F12/26C08F12/32C08F12/34Y02P20/584B01J23/464B01J31/08B01J31/4046B01J31/2239B01J31/1658B01J2231/34B01J2531/0219B01J2531/822C08F212/22C08F212/32C08F212/34C08F212/36C08F212/26B01J31/06C08F4/65916C08F20/18B01J31/28C08J9/0061C08J9/141C08J9/142C08J9/145C08J9/149C08J2203/12C08J2203/14C08J2203/142C08J2325/08C08J2405/00C08J2429/04
Inventor 洪浩李九远董长明张欣詹姆斯·盖吉
Owner ASYMCHEM LAB TIANJIN
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