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Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof

A kind of technology of pyridoxamine and catalyst, applied in the field of novel chiral open-chain pyridoxamine catalyst and its synthesis

Inactive Publication Date: 2016-11-09
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 yet attracted the attention of chemists.

Method used

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  • Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof
  • Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof
  • Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Compound 5a (R 1 = R 2 =H) Synthesis

[0057]

[0058] Compound 4a (30.00g, 172.42mmol, 1.0eq.) was dissolved in 500mL freshly distilled THF (1000mL reaction flask), and triethylamine (49.8mL, 344.85mmol, 2.0eq.) and MOM-Cl (19.6mL, 258.64mmol, 1.5eq.), naturally return to room temperature under stirring. TLC tracking and monitoring, after 1h, the reaction of compound 4a was complete. After the solvent was rotated, 200mL of water and 200mL of ethyl acetate were added for extraction, and the aqueous phase continued to be extracted with ethyl acetate (50mL x3). 2 SO 4 After drying for 6 hours, filter, spin the filtrate to dryness, and obtain compound 5a (colorless liquid, 33.45 g, yield 89.0%) by column chromatography.

[0059] Colorless oil, IR (KBr) 1576, 1557, 1448, 1427, 1250cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ8.38-8.32 (m, 2H), 7.56 (t, J = 2.0Hz, 1H), 5.19 (s, 2H), 3.48 (s, 3H); 13 C NMR (100MHz, CDCl 3 )δ153.9, 144.1, 138.0, 125.9, 120.3, 94.8, 56.4; HRMS...

Embodiment 2

[0064] Compound 6a (R 1 = R 2 =H) Synthesis

[0065]

[0066] Replace the dry 1000mL reaction flask with stirring bar with N 2 Three times, inject 100mL of freshly distilled THF at -78°C, and then inject diisopropylamine (11.7mL, 82.95mmol, 1.2eq.) and n-butyllithium solution (1.6M in hexane, 49.7mL, 79.45mmol, 1.15eq. ), after stirring at -78°C for 30min, slowly inject 100mL of compound 5a (15.00g, 69.12mmol, 1.0eq.) in THF solution, keep stirring at -78°C for 1h, inject ethyl formate (11.1mL, 138.25mmol, 2.1eq.) Keep stirring at -78°C. TLC tracking monitoring, compound 5a reacted completely after 3h, added 50mL saturated NaHCO 3 The reaction was quenched by the solution, the solvent was spun off, and 150mL of water and 150mL of ethyl acetate were added for extraction, and the aqueous phase was continuously extracted with ethyl acetate (100mL x3), and the organic phases were combined and washed with anhydrous Na 2 SO 4 After drying for 6 hours, filter, spin the filtr...

Embodiment 2-3

[0071] Except that the molar ratio of compound 5a, diisopropylamine, tert-butyllithium and ethyl formate is 1:1.5:1.5:2.5, the reaction temperature is -70°C, and the reaction time is 3h, the rest are the same as in Example 2. Example 3

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Abstract

The invention relates to a novel chiral open-chain pyridoxamine catalyst and a synthesis method and application thereof. The structural general formula of the pyridoxamine catalyst is shown in the specification, wherein R1, R2, R3 and R4 are one of hydrogen, C1-24 alkyl, C1-24 alkyl containing substituent groups, substances shown in the specification and halogen, the substituent groups on C1-24 alkyl are a substance shown in the specification or a substance shown in the specification or a substance shown in the specification or O-Rw or S-Rw' or halogen, and Rx, Rx', Ry, Ry', Ry'', Rz, Rz', Rw and Rw' 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 halogen. Compared with the prior art, the pyridoxamine catalyst can achieve rapid and efficient synthesis of chiral amino acid, the preparation raw materials are easy to obtain, reaction conditions are mild, cost is low, and when the novel chiral open-chain pyridoxamine catalyst is used for a transamination reaction, the conditions are mild, and the reaction is stable.

Description

technical field [0001] The invention relates to the field of catalyst synthesis, in particular to a novel chiral open-chain pyridoxamine catalyst and its synthesis method and application. Background technique [0002] An important pathway for the formation of chiral α-amino acids in organisms is the transamination reaction of α-keto acids catalyzed by transaminases. In this process, vitamin B6 (pyridoxal and pyridoxamine) acts as a coenzyme and cooperates with the transaminase in the organism to complete the process, and the reaction center is vitamin B6. In this reaction, 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, while the original amino acid is converted into α-keto acid [D.Zhu and L.Hua , Biotechnol. J., 2009, 4, 1420]. Based on the skeleton of vitamin B6, the research work of biomimetic transamination has been paid attention to by chemists very early. In 1952, the Snell researc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/66B01J31/02C07C229/08C07C227/08
CPCC07D213/66B01J31/0244B01J2231/4283C07C227/08C07C229/08
Inventor 赵宝国陈剑锋赵濬宇龚幸
Owner SHANGHAI NORMAL UNIVERSITY
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