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Gamma-amino acid analogue and synthesis method thereof

A synthesis method, amino acid technology, applied in peptide preparation methods, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of low atom economy and large-scale reactions, and achieve wide selectivity of reaction substrates and cheap raw materials Easy to obtain and mild reaction conditions

Active Publication Date: 2021-02-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This leads to lower atom economy and potential safety issues for large-scale reactions

Method used

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  • Gamma-amino acid analogue and synthesis method thereof
  • Gamma-amino acid analogue and synthesis method thereof
  • Gamma-amino acid analogue and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A preferred embodiment of the present invention provides a method for synthesizing γ-amino acid analogues, the specific steps are as follows:

[0041]

[0042] S1: To a dry Schlenk tube (10 mL), add 1 (0.3 mmol, 1.0 equiv), Ir[dF(CF 3 )(ppy)] 2 (dtbbpy)·PF 6 (3.3mg, 0.003mmol, 1mol%), 2a (97.3mg, 0.39mmol, 1.3eq)

[0043] S2: add Cs again 2 CO 3 (147.0mg, 0.45mmol, 1.5 equiv)

[0044] S3: Then vacuumize and replace nitrogen for 3 times. Then in N 2 DMF (2.5 mL) was added under atmosphere.

[0045] S4: Seal the Schlenk tube, stir the reaction in a water bath, and irradiate it with a 30W blue LED light (3cm away, with a cooling fan to keep the reaction temperature at 25-30°C) for 8 hours.

[0046] S5: After the reaction, use 1ml 2N HCl (aq.), 2ml H 2 O was quenched, diluted with 3ml EtOAc, stirred for 10 min, extracted 5 times with EtOAc, and the combined organic phase was concentrated in vacuo.

[0047] S6: Finally, the product is purified by silica gel colu...

Embodiment 2

[0049] A preferred embodiment of the present invention provides a method for synthesizing γ-amino acid analogues, the specific steps are as follows:

[0050]

[0051] S1: To a dry Schlenk tube (10 mL), add 1a (0.3 mmol, 1.0 equiv), Ir[dF(CF 3 )(ppy)] 2 (dtbbpy)·PF 6 (1.7mg, 0.0015mmol, 0.5mol%), 2 (0.45mmol, 1.5eq)

[0052] S2: add CsF (91.2mg, 0.6mmol, 2.0 equiv)

[0053] S3: Then vacuumize and replace nitrogen for 3 times. Then in N 2 DMA (3 mL) was added under atmosphere.

[0054] S4: Seal the Schlenk tube, stir the reaction in a water bath, and irradiate it with a 30W blue LED light (3cm away, with a cooling fan to keep the reaction temperature at 25-30°C) for 8 hours.

[0055] S5: After the reaction, use 1ml 2N HCl (aq.), 2ml H 2 O was quenched, diluted with 3ml EtOAc, stirred for 10 min, extracted 5 times with EtOAc, and the combined organic phase was concentrated in vacuo.

[0056] S6: Finally, the product is purified by silica gel column chromatography (petr...

Embodiment 3

[0058] A preferred embodiment of the present invention provides a method for synthesizing γ-amino acid analogues, the specific steps are as follows:

[0059]

[0060] S1: To a dry Schlenk tube (10 mL), add 1a (0.3 mmol, 1.0 equiv), Ir[dF(CF 3 )(ppy)] 2 (dtbbpy)·PF 6 (1.7 mg, 0.0015 mmol, 0.5 mol%), 2a (0.45 mmol, 1.5 equiv).

[0061] S2: add CsF (137mg, 0.9mmol, 3.0eq); add molecular sieves (200mg).

[0062] S3: Then vacuumize and replace nitrogen for 3 times. Then in N 2 DMA (3 mL) was added under atmosphere.

[0063] S4: Seal the Schlenk tube, stir the reaction in a water bath, and irradiate it with a 30W blue LED light (3cm away, with a cooling fan to keep the reaction temperature at 25-30°C) for 8 hours.

[0064] S5: After the reaction, use 1ml 2N HCl (aq.), 2ml H 2 O was quenched, diluted with 3ml EtOAc, stirred for 10 min, extracted 5 times with EtOAc, and the combined organic phase was concentrated in vacuo.

[0065] S6: Finally, the product is purified by si...

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Abstract

The method discloses a gamma-amino acid analogue and a synthesis method thereof. The method comprises the following steps of adding a photosensitizer, alkali and carboxylic acid into a dry reaction tube, adding a solvent and a reaction substrate under the atmosphere of protective gas, reacting under the irradiation of visible light, carrying out acidification quenching treatment on the mixture obtained by the reaction after the reaction of the raw materials is finished, and separating and purifying to obtain a product gamma-amino acid analogue. The photosensitizer comprises Ir[dF(CF3)(ppy)]2(dtbbpy).PF6, Ir(ppy)2(dbbpy).PF6, 4CzIPN, and the alkali is cesium fluoride, cesium carbonate or potassium fluoride; the additive is a molecular sieve; and the reaction substrate is an alkene compound.The gamma-amino acid analogue is efficiently and highly selectively synthesized under the atmosphere of visible light induction and protective gas. According to the scheme, reaction conditions are mild, reaction substrate selectivity is wide, and the reaction substrate selectivity is amplified to the gram-level scale.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a gamma-amino acid analog and a synthesis method thereof. Background technique [0002] γ-amino acid is an important class of amino acids. Taking γ-aminobutyric acid as an example, it is an important inhibitory neurotransmitter in the mammalian central nervous system. related to mental illness. γ-aminobutyric acid transaminase continuously metabolizes γ-aminobutyric acid in the animal brain, and when it decreases to a certain value, it will lead to epilepsy and other diseases. And γ-aminobutyric acid analogs with good fat solubility and physiological activity exist in many drug molecules. In recent decades, a series of γ-aminobutyric acid drugs represented by baclofen have developed unprecedentedly rapidly , a wide variety and new derivatives appear as new drugs continuously, indicating that the market prospect of GABA drugs is broad. However, in the synt...

Claims

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Application Information

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IPC IPC(8): C07D207/08C07D405/06C07J43/00C07D207/12C07D207/26C07D211/34C07D265/30C07D207/267C07D209/52C07K5/02C07K1/02C07K1/16
CPCC07D207/08C07D405/06C07J43/00C07D207/12C07D207/26C07D211/34C07D265/30C07D207/267C07D209/52C07K5/02C07B2200/07
Inventor 余达刚廖黎丽曹光梅蒋元旭靳兴浩胡鑫龙柯杰森孙国权贵永远
Owner SICHUAN UNIV
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