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Method for synthesizing non-natural amino acid through photo-induced anion catalysis

A technology of non-natural amino acids and synthetic methods, applied in the field of organic compound synthesis, can solve the problems of limited industrial application and narrow substrate range, and achieve the effects of good compatibility, high conversion rate, large chemical value and application prospect.

Active Publication Date: 2020-06-12
UNIV OF SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently developed methods mainly have a narrow range of substrates and require strong oxidants or transition metals and complex ligands, which greatly limit their industrial application.

Method used

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  • Method for synthesizing non-natural amino acid through photo-induced anion catalysis
  • Method for synthesizing non-natural amino acid through photo-induced anion catalysis
  • Method for synthesizing non-natural amino acid through photo-induced anion catalysis

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preparation example Construction

[0015] Specifically, according to some embodiments of the present invention, a method for synthesizing a light-induced anion-catalyzed unnatural amino acid is provided, comprising the following steps:

[0016] Under the condition that iodonium salt and organic solvent exist, the active carboxylic acid ester shown in formula (1) is reacted with the glycine derivative shown in formula (2) under visible light, obtains the alkyl group shown in formula (3) Chemicalized compounds:

[0017]

[0018] where, where, R 1 Is a substituted or unsubstituted C1~C20 alkyl group or a substituted or unsubstituted C3~C20 cycloalkyl group; R 2 for OR 4 or NR 5 , R 4 Selected from C1~C20 alkyl, R 5 R 3 Represents a single substituent to the maximum permissible substituent, selected from hydrogen or chlorine; Ar is a substituted or unsubstituted C6-C20 aryl group; when the above-mentioned substituted or unsubstituted groups have substituents, the substituents are boron esters Base, acetal...

Embodiment 1

[0039] Embodiment 1, preparation 2-cyclohexyl-2-(phenylamino) ethyl acetate (1)

[0040] Reaction formula:

[0041]

[0042] The specific method is as follows:

[0043] Add tetrahexylammonium iodide (20mol%, 14mg), NHPI cyclohexylcarboxylate (0.3mmol ) and N-phenylglycine ethyl ester (0.2 mmol). The air in the tube was completely replaced with argon three times, and then 1 mL of N,N-dimethylacetamide was added under an argon atmosphere. The reaction system was continuously stirred at room temperature for 24 hours under the irradiation of a 40W purple LED (427nm) lamp (IKA magnetic stirrer, RCT basic type, stirring speed 500 rpm). After the reaction is complete, use H 2 The reaction was quenched with O, and the reaction solution was extracted with ethyl acetate (3*10 mL), and then the combined organic phase was concentrated by rotary evaporation (BUCHI Co., Ltd., BUCHI rotary evaporator R-3). The concentrated residue is passed through a chromatographic column (Beijing X...

Embodiment 2

[0047] Example 2, 2-cyclohexyl-2-((4-methoxyphenyl) amino) ethyl acetate (2)

[0048] Reaction formula:

[0049]

[0050] The method is the same as in Example 1, the difference lies in the type of glycine derivative shown in the above formula, and the yield is shown in Table 1.

[0051] Gained product is carried out nuclear magnetic resonance analysis, the result is as follows:

[0052] 1 H NMR (400MHz, CDCl 3 )δ6.79–6.72(m,2H),6.64–6.58(m,2H),4.17–4.12(m,2H),3.79–3.69(m,4H),1.89–1.65(m,6H),1.28– 1.08(m,8H).

[0053] 13 C NMR (101MHz, CDCl 3 )δ173.9, 152.7, 141.4, 115.3, 114.8, 63.5, 60.7, 55.7, 41.2, 29.6, 29.2, 26.3, 26.2, 26.0, 14.3.

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Abstract

The invention relates to a method for synthesizing non-natural amino acids through photo-induced anion catalysis. The method comprises the following step: in the presence of iodized salt and an organic solvent, reacting active carboxylic ester with a glycine derivative through visible light illumination to obtain a series of non-natural amino acids. According to the method, visible light catalysisis utilized, reaction conditions are mild and operation is easy; compared with the traditional method reported before, the method has the advantages that the use of the noble metal catalyst is avoided, the requirement of developing green environment-friendly chemistry is met, the substrate range is wide and the functional group compatibility is good; and the method can be successfully applied togram-scale amplification experiments and is high in reaction conversion rate and has industrial synthesis value prospects.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a method for synthesizing unnatural amino acids catalyzed by light-induced anions. Background technique [0002] Synthesizing unnatural amino acids or modifying natural amino acids is one of the common methods for the synthesis of polypeptide drugs. Among them, glycine and its derivatives undergo nitrogen atom α-C(sp 3 )-H alkylation is one of the most straightforward methods. The currently developed methods mainly have a narrow range of substrates and require strong oxidants or transition metals and complex ligands, which greatly limit their industrial applications. Contents of the invention [0003] In view of this, the main purpose of the present invention is to provide a photo-induced anion-catalyzed unnatural amino acid synthesis method, in order to at least partially solve at least one of the above-mentioned technical problems. [0004] In order to achieve the...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C229/28C07F5/02C07D317/66C07C231/12C07C237/14C07C319/20C07C323/59C07D207/16C07C229/18C07C229/30C07C229/42C07K5/087
CPCC07C227/16C07C231/12C07C319/20C07D207/16C07D317/66C07F5/025C07K5/0812C07C2601/04C07C2601/08C07C2601/14C07C2603/74C07C229/28C07C229/18C07C229/30C07C229/42C07C237/14C07C323/59
Inventor 傅尧王光祖尚睿赵斌
Owner UNIV OF SCI & TECH OF CHINA
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