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Novel biaryl-structured chiral N-methyl pyridoxal catalyst and synthesis and application thereof

A methyl pyridoxal and catalyst technology, applied in catalytic reaction, physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, etc., can solve the problem of α-β-diamino acid derivatives, etc.

Active Publication Date: 2018-12-07
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, there is still no relevant public literature report on chiral small molecule pyridoxal and its derivatives as catalysts for the synthesis of chiral α-β-diamino acid derivatives

Method used

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  • Novel biaryl-structured chiral N-methyl pyridoxal catalyst and synthesis and application thereof
  • Novel biaryl-structured chiral N-methyl pyridoxal catalyst and synthesis and application thereof
  • Novel biaryl-structured chiral N-methyl pyridoxal catalyst and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The synthesis of embodiment 1 compound 7:

[0064]

[0065] Add compound 5 (2.00g, 7.69mmol), compound 6 (2.31g, 11.54mmol), palladium complex (0.158g, 0.19mmol), ligand Ruphos (0.358g, 0.77mmol) and KF (1.34g, 23.07mmol), add a stirring bar, cover the rubber stopper, replace N 2 Three times, then inject 1,4-dioxane (20 mL) and water (2.5 mL) by syringe. After the reaction system was stirred at room temperature for 30 minutes, it was transferred to 100° C. and stirred overnight. Cool to room temperature, filter, concentrate the filtrate, and obtain compound 7 (yellow oily liquid, 0.93 g, yield 36%) by column chromatography.

[0066] Yellow oil; 1 H NMR (400MHz, CDCl 3 )δ10.19(s,1H),9.82(s,1H),8.82(s,1H),8.07(d,J=8.8Hz,1H),8.01(d,J=8.8Hz,1H),7.96( d, J=8.4Hz, 1H), 7.63(t, J=7.6Hz, 1H), 7.44(t, J=8.0Hz, 1H), 7.27(d, J=7.2Hz, 1H), 5.41(s, 2H), 3.60(s,3H), 2.07(s,3H).

Embodiment 1-1

[0068] Compared with Example 1, except that the molar ratio of compound 5 and compound 6 was replaced by 1:1, and the reaction conditions were replaced by: reaction temperature -20°C, reaction time 24h, the rest were the same.

Embodiment 1-2

[0070] Compared with Example 1, except that the molar ratio of Compound 5 and Compound 6 was replaced by 1:5, and the reaction conditions were replaced by: reaction temperature 120° C., reaction time 1 h, the rest were the same.

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Abstract

The invention relates to a novel biaryl-structured chiral N-methyl pyridoxal catalyst and synthesis and application thereof. The general structural formula is as shown in the specification, wherein R1is hydrogen or C1-C24 alkyl, and R2 and R3 are independently hydrogen or C1-C24 alkyl. In comparison with the prior art, the prepared pyridoxal catalyst can be used in a bionic Mannich reaction process, and fast and effective synthesis of a chiral alpha-beta-diamino acid derivative is realized.

Description

technical field [0001] The invention belongs to the technical field of high-resolution catalysts, and relates to a novel biaryl structure chiral N-methylpyridoxal catalyst and its synthesis and application. Background technique [0002] In organisms, compounds containing free amino groups can directly participate in the reaction. For example, enzyme-catalyzed glycine can directly add electrophiles (such as aldehydes) to generate β-carboxy α-amino acids. The reaction conditions are mild, and glycine directly participates in the reaction , without any protecting group. In this reaction, the active center of the enzyme is vitamin B6, which exists in the form of phosphoric acid (PMP and PLP) in the body. It is a water-soluble vitamin and its main function is to participate in various enzyme-catalyzed reactions as a coenzyme factor. The chemists found that pyridoxal can also induce the addition of glycine to aldehydes in the absence of enzymes. The Kuzuhara and Breslow research...

Claims

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Application Information

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IPC IPC(8): C07D213/64B01J31/02C07B37/02C07F9/36C07F9/58C07F9/6503C07F9/655C07F9/6553C07F9/6561C07J1/00
CPCB01J31/0244B01J31/0271B01J2231/341C07B37/02C07D213/64C07F9/36C07F9/65515C07F9/655345C07F9/6561C07J1/00
Inventor 赵宝国陈剑锋龚幸
Owner SHANGHAI NORMAL UNIVERSITY
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