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Chiral pyridoxamine catalyst as well as synthesis method and application thereof

A catalyst, pyridoxamine technology, applied in the direction of organic chemistry methods, chemical instruments and methods, physical/chemical process catalysts, etc.

Active Publication Date: 2016-11-16
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the use of chiral small molecules pyridoxal and its derivatives as catalysts to catalyze the synthesis of chiral α-amino acids has not been paid attention to by chemists.

Method used

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  • Chiral pyridoxamine catalyst as well as synthesis method and application thereof
  • Chiral pyridoxamine catalyst as well as synthesis method and application thereof
  • Chiral pyridoxamine catalyst as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1: Intermediate 2a (R 2 =R 3 =R 4 =R 5 =H) Synthesis.

[0079]

[0080] Weigh glycine ethyl ester hydrochloride (100.0g, 716.4mmol) in 1000mL DCM (2000mL reaction bottle), add triethylamine (145.2g, 1434.8mmol) under ice bath, after stirring evenly, the constant pressure dropping funnel slowly drops Add succinic acid monoethyl chloride (100 mL, 716.3 mmol), drop it over 30 minutes, and return to room temperature naturally under continuous stirring. TLC tracking monitoring, the reaction is complete after 4h, add 300mL water for extraction, continue to add saturated NaHCO to the organic phase 3 (300mL x2) extraction, the organic phase was dried with anhydrous Na2SO4 for 6h, filtered, and the filtrate was spin-dried to obtain intermediate 2a (white solid, 170.00g, yield 97%). White solid; m.p.72-73℃; IR(KBr)3321,1748,1734,1655,1552,1212cm -1 ; 1 H NMR (600MHz, CDCl 3)δ6.29(s,1H),4.19(q,J=7.2Hz,2H),4.12(q,J=7.2Hz,2H),4.00(d,J=4.8Hz,2H),2.65(t, J=6.6Hz, 2...

Embodiment 1-1

[0082] Example 1-1: except that the molar ratio of glycine ethyl ester hydrochloride, triethylamine and succinic acid monoethyl chloride is 1:1:6, the reaction temperature is -20°C, and the reaction time is 24h, All the other are the same as in Example 1.

Embodiment 1-2

[0083] Example 1-2: Except that the molar ratio of glycine ethyl ester hydrochloride, triethylamine and succinic acid monoethyl chloride is 1:6:3, the reaction temperature is 50°C, and the reaction time is 1h, the rest All the same as in Example 1.

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Abstract

The invention relates to a chiral pyridoxamine catalyst as well as a synthesis method and an application thereof. The chiral pyridoxamine catalyst adopts the structure shown in the general structural formula (R-1) or the general structural formula (S-1) which are shown in the specification; R<1>, R<2>, R<3>, R<4> and R<5> are one of hydrogen, alkyl of C1-C24, C1-C24 alkyl containing substituent groups, a compound I shown in the specification, a compound II shown in the specification, a compound III shown in the specification, O-R<w>, S-R<W'> and halogens; the substituent groups are the compound I shown in the specification, the compound II shown in the specification, the compound III shown in the specification, O-R<w>, S-R<W'> or the halogens; R<x>, R<x'>, R<y>, R<y'>, R<y''>, R<z>, R<z'>, R<w> and R<w'> are one of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, benzyl, (1-phenyl) ethyl, 1-naphthyl, 2-naphthyl and halogens. Compared with the prior art, the catalyst as well as the synthesis method and the application thereof have the advantages that reaction conditions are mild, operation is easy, repeatability is good, the ee value and the yield are relatively high when the prepared catalyst is used for synthesizing alpha-amino acid, and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a chiral pyridoxamine catalyst and its synthesis method and application. Background technique [0002] Amino acids in organisms are mainly realized through the transamination of ketoacids under the action of transaminases, which is a very important biological process. Transaminase transfers the α-amino group of one amino acid to the carbonyl group of another α-keto acid to generate a new amino acid [D.Zhu and L.Hua, Biotechnol.J., 2009, 4, 420]; at the same time, the original amino acid It is transformed into α-keto acid, and its reaction center is vitamin B 6 , namely pyridoxal and its derivatives. [0003] Pyridoxal (PL) participates in many metabolic activities. It can be used as a coenzyme in the synthesis of amino acids [D.Zhu and L.Hua, Biotechnol.J., 2009, 4, 1420.], and it can also be used as a vitamin in vitro. B 6 It can catalyze the transamination of α-ke...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07D221/04C07C227/32C07C229/08C07C229/30C07C229/22C07C229/34C07C229/24C07D307/79
CPCB01J31/0247C07B2200/07C07C227/32C07D221/04C07D307/79C07C229/08C07C229/30C07C229/22C07C229/34C07C229/24
Inventor 赵宝国兰晓宇陶创安刘旭亮
Owner SHANGHAI NORMAL UNIVERSITY
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