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Preparing method and application of chiral imidazolinone fungicide decorated by peptide loded with silica gel

An imidazolinone, amino acid technology, applied in the preparation of carbon-based compounds, the preparation of organic compounds, catalysts for physical/chemical processes, etc. Enantioselectivity, simple process effect

Inactive Publication Date: 2007-09-19
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The previous technology loaded chiral imidazolinone on polyethylene glycol (PEG) (Adv.Synth.Catal., 2002, 344, 149), silica gel (Adv.Synth.Catal., 2006, 348, 2027) or resin (Adv.Synth.Catal., 2002,344,941), and in the ionic liquid (Adv.Synth.Catal., 2004,346,49) to investigate the recycling of the catalyst, after some loads directly cause the catalyst to Enantioselectivity decreases, and enantioselectivity will decrease significantly after some supported catalysts are recycled for more than 3 times

Method used

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  • Preparing method and application of chiral imidazolinone fungicide decorated by peptide loded with silica gel
  • Preparing method and application of chiral imidazolinone fungicide decorated by peptide loded with silica gel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of a chiral imidazolinone modified with pentameric amino acid loaded on silica gel, the chiral imidazolinone modified with pentameric amino acid loaded on silica gel is the chiral imidazolinone kind of.

[0030] In the first step, 180 g of 25% aqueous solution of methylamine was added to 50 g of raw material 1 tyrosine methyl ester hydrochloride to obtain 47 g of white solid crude product 2, (S)-N-methyl-2-amino-3 -(4-(hydroxyl)phenyl)-propionamide; in the second step, add 60g of acetone, 90g of methanol, and 0.5g of p-toluenesulfonic acid to the crude product 2 to obtain the crude product 3 chiral imidazolidinone , productive rate 50%; In the 3rd step, add the acetone of 90g, the K of 18g successively to crude product 3 2 CO 3, 35g of methyl p-bromomethylbenzoate, to obtain intermediate product 4, (s)-methyl-4((4-((1,2,2-trimethyl-5-oxoimidazolidine-4-alkane Base) methyl)-phenoxy) methyl) benzoate, productive rate 50%; In the 4th step, get the...

Embodiment 2

[0031] Example 2: Preparation of a chiral imidazolinone catalyst modified with octameric leuco amino acid loaded on silica gel, the chiral imidazolinone modified with octameric amino acid loaded on silica gel is a chiral imidazolinone modified with oligomeric amino acid loaded on silica gel One of.

[0032] In the first step, 180 g of 25% aqueous solution of methylamine was added to 50 g of raw material 1 tyrosine methyl ester hydrochloride to obtain 47 g of white solid crude product 2, (S)-N-methyl-2-amino-3 -(4-(hydroxyl)phenyl)-propionamide; in the second step, add 60g of acetone, 90g of methanol, and 0.5g of p-toluenesulfonic acid to the crude product 2 to obtain the crude product 3 chiral imidazolidinone , productive rate 50%; In the 3rd step, add the acetone of 90g, the K of 18g successively to crude product 3 2 CO 3 , 35g of methyl p-bromomethylbenzoate, to obtain intermediate product 4, (s)-methyl-4((4-((1,2,2-trimethyl-5-oxoimidazolidine-4-alkane Base) methyl)-phen...

Embodiment 3

[0033] Example 3: Preparation of a chiral imidazolinone catalyst modified by silica gel-loaded decamerine amino acid, the chiral imidazolinone modified by silica gel-loaded decamerine amino acid is a chiral imidazolinone modified by silica gel-loaded oligomeric amino acid One of.

[0034] In the first step, to 5.0 g of raw material 1 tyrosine methyl ester hydrochloride, add 18 g of methylamine 25% aqueous solution to obtain 4.8 g of white solid crude product 2, (S)-N-methyl-2-amino -3-(4-(hydroxyl) phenyl)-propionamide; Conversion rate 100%; In the second step, add the acetone of 6.0g, the methyl alcohol of 9.0g, the p-toluenesulfonic acid of 0.5g in the crude product 2, Get crude product 3 chiral imidazolinones, productive rate 55%; In the 3rd step, add the acetone of 18g, the K of 3.6g successively to crude product 3 2 CO 3 , 7.0g of methyl p-bromomethylbenzoate to obtain intermediate product 4: (s)-methyl-4((4-((1,2,2-trimethyl-5-oximidazolidine-4- Alkyl) methyl)-phenoxy...

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Abstract

The present invention discloses a preparation method of chirality imidazolinone which is supported by silica gel and is modified by oligoamino acid, more specifially, the present invention discloses a friend-environment type chirality organic catalyst which can be circularly used in the asymmetric Diels-Alder reaction, and belongs to the catalyst preparation and application technology field. The NCA polymerisation of a plurality of amino acid is initiated by using chirality imidazolinone as initiator, and the polymeric amino acid has excellent adhesion property on silicon gel, so that the chirality imidazolinone catalyst can be effectively solid supported on the silicon gel surface by means of the adhesion property of the polymeric amino acid, and then the product is obtained. The obtained product is especially adapted to be used as catalyst in asymmetric Diels-Alder addition reaction, and has excellent catalytic activity and antipode selectivity which is up to 96% ee, furthermore the catalyst can be recovered for circular use.

Description

technical field [0001] The present invention relates to the preparation and application of a chiral imidazolinone modified by oligomeric amino acid loaded on silica gel. The application refers to the asymmetric cycloaddition of the immobilized chiral imidazolinone in conjugated diene and cinnamaldehyde The invention relates to a catalyst which can be recycled in the reaction (Diels-Alder), and belongs to the technical field of catalyst preparation and application. Background technique [0002] Chiral imidazolinones are widely used in the synthesis of chiral compounds, with good catalytic effect and high selectivity. For example, it can efficiently catalyze Diel-Alder reaction, Friedel-Crafts alkylation, α-chlorination of aldehydes, hydrogenation reduction, and conjugate addition of amines. The use of chiral imidazolinone as a catalyst for the reaction eliminates the heavy metal pollution of general metal catalysts, and has the advantages of high s...

Claims

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Application Information

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IPC IPC(8): B01J31/06B01J31/02C07B37/12C07C45/67
Inventor 邹刚申朝辉张瑞雪杨小根汤杰
Owner EAST CHINA NORMAL UNIVERSITY
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