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Hydrazine modification method of visible light induced glycine derivative

A modification method, glycine technology, which is applied in the field of hydrazine modification of glycine derivatives induced by visible light, can solve the problems of narrow substrate range and limited industrial application, and achieve high selectivity, no catalyst and additives, and high atom utilization. Effect

Active Publication Date: 2021-08-24
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • 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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  • Hydrazine modification method of visible light induced glycine derivative
  • Hydrazine modification method of visible light induced glycine derivative
  • Hydrazine modification method of visible light induced glycine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Reaction formula:

[0040]

[0041] The specific method is as follows: Add azobis-tert-butyl ester (0.3 mmol) and N-phenylglycine to a 10 mL Schlenk reaction tube (Beijing Xinweier Glass Instrument Co., Ltd., F891410 reaction tube, capacity 10 mL, ground 14 / 20) Ethyl ester (0.2 mmol). The air in the tube was completely replaced with argon three times, and then 1 mL of acetonitrile was added under an argon atmosphere. The reaction system was continuously stirred at room temperature for 12 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 Xinweier Glass I...

Embodiment 2

[0047] Reaction formula:

[0048]

[0049] 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.

[0050] Gained product is carried out nuclear magnetic resonance analysis, the result is as follows:

[0051] 1 H NMR (400MHz, CDCl 3 )δ6.72-6.66 (m, 4H), 6.30-5.79 (m, 2H), 4.18 (d, J=7.0Hz, 2H), 3.67 (s, 3H), 1.50-1.32 (m, 18H), 1.26 (t, J=7.1Hz, 3H).

[0052] 13 C NMR (101MHz, CDCl 3 )δ167.8, 154.6, 153.2, 137.8, 115.2, 114.9, 82.1, 81.2, 65.9, 62.2, 55.7, 28.1, 27.9, 14.0.

[0053] HRMS (ESI) calcd for C 21 h 34 N 3 o 7 + [M+H] + :440.2391, found: 440.2394.

Embodiment 3

[0055] Reaction formula:

[0056]

[0057] 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.

[0058] Gained product is carried out nuclear magnetic resonance analysis, the result is as follows:

[0059] 1 H NMR (400MHz, CDCl 3 )δ6.90(t, J=8.6Hz, 2H), 6.71(s, 2H), 6.14-5.93(m, 2H), 4.25-4.21(m, 2H), 1.60-1.30(m, 21H).

[0060] 13 C NMR (101MHz, CDCl 3 )δ167.8, 156.7(d, J=236.9Hz), 140.3, 123.4(d, J=8.7Hz), 115.8(d, J=22.4Hz), 114.9, 82.3, 81.4, 66.0, 62.4, 28.1, 27.9 , 14.0.

[0061] HRMS (ESI) calcd for C 20 h 31 FN 3 o 6 + [M+H] + : 428.2191, found: 428.2195.

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Abstract

The invention relates to a hydrazine modification method of a visible light induced glycine derivative. The method comprises the following steps: in the presence of an organic solvent, an azo compound and a glycine derivative are subjected to a reaction through visible light excitation, and a series of non-natural amino acids can be obtained. According to the method provided by the invention, visible light catalysis is utilized, the reaction condition is mild, the atom economy is high, and compared with a traditional method reported before, the method avoids the use of a catalyst and an additive, meets the requirements of developing green and environment-friendly chemistry, and is wide in substrate range and good in functional group compatibility; the method can be successfully applied to gram-scale amplification experiments, 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 visible light-induced hydrazine modification method of glycine derivatives. 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 functionalization is one of the most straightforward approaches. 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 visible light-induced hydrazine modification method of glycine derivatives, in order to at least partially solve at least one of the above-mentioned technical problems. [0004] In order to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/068C07K5/09C07C281/02C07F5/02
CPCC07K5/06086C07K5/0815C07C281/02C07F5/025Y02P20/55
Inventor 石景刘梦婷王光祖
Owner UNIV OF SCI & TECH OF CHINA
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