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Synthesis method of alpha-hydroxyl beta-nitroamide compound

A synthesis method and technology of nitroamides, which are applied in the preparation of organic compounds, chemical instruments and methods, separation/purification of carboxylic acid amides, etc., can solve problems that have not been reported, and achieve environmental friendliness, wide sources, and cheap prices Effect

Pending Publication Date: 2022-02-01
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Natural amino acids are widely sourced, cheap, and environmentally friendly, but their application in catalyzing the Henry reaction has not been reported.

Method used

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  • Synthesis method of alpha-hydroxyl beta-nitroamide compound
  • Synthesis method of alpha-hydroxyl beta-nitroamide compound
  • Synthesis method of alpha-hydroxyl beta-nitroamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-14

[0024] Embodiment 1-14 reaction condition optimization test

[0025] Using the α-ketoamide compound shown in formula 1a as the reaction substrate, and reacting with nitromethane to prepare the α-hydroxyl β-nitroamide compound shown in formula 3a, the effect of different synthesis conditions on the yield of the target product was discussed. The results are shown in Table 1. The reaction formula is as follows:

[0026]

[0027] Taking Example 10 as an example, the typical reaction operation is as follows:

[0028] Add α-ketoamide compound (0.1mmol), L-arginine (0.02mmol), nitromethane (2mmol) and water (1mL) successively to reactor shown in formula 1a, then place reactor in The reaction was stirred at room temperature for 6 hours. After the completion of the reaction was monitored by TLC, dichloromethane (30 mL*3) was added to the reaction mixture for extraction, the organic phases were combined, dried by adding anhydrous sodium sulfate, and concentrated in vacuo to obtain ...

Embodiment 15-36

[0039] Embodiment 15-36 reaction substrate expansion test

[0040] Taking the reaction conditions of Example 10 as the optimal reaction conditions, further explored the adaptability to the reaction substrate under the optimal reaction conditions, that is, only changing the type of reaction raw materials, and the rest of the reaction conditions and operations are the same as in Example 10, the results are as follows :

[0041]

[0042] Structural characterization of the product:

[0043] Compound 3b: white solid (31.0 mg, 97%). 1 H NMR (400MHz, CDCl 3 )δ8.30(s,1H),7.74–7.67(m,1H),7.62–7.54(m,2H),7.53–7.46(m,1H),7.45–7.33(m,4H),7.19(t, J=7.5Hz, 1H), 5.42(d, J=14.0Hz, 1H), 5.28(d, J=14.0Hz, 1H), 5.11(s, 1H). 13 C NMR (126MHz, CDCl 3 ) δ 167.16, 136.81, 133.49, 132.34, 132.12, 130.97, 129.12, 129.09, 127.77, 125.17, 120.12, 78.87.

[0044] Compound 3c: white solid (31.3 mg, 98%). 1 H NMR (500MHz, CDCl 3 )δ8.46(s,1H),7.72(s,1H),7.56-7.49(m,3H),7.37-7.30(m,4H),7.13(t,J=7....

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Abstract

The invention discloses a novel method for preparing an alpha-hydroxyl beta-nitro amide compound through a Henry reaction catalyzed by L-arginine in a water phase. According to the method, an alpha-ketoamide compound and nitromethane are used as reaction raw materials, natural amino acid is used as a catalyst, water is used as a reaction solvent, and the alpha-hydroxyl beta-nitroamide compound is prepared through reaction under the room temperature condition. The method is mild and simple in reaction condition, economical and cheap, wide in reaction substrate application range and excellent in target product yield.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing α-hydroxyl β-nitroamide compounds. Background technique [0002] The nitroalcohol condensation of carbonyl compounds and nitroalkanes under the action of a base is called the Henry reaction, which is a very important organic reaction for building C-C bonds in organic synthesis reactions, and is widely used in pharmaceutical intermediates and natural The synthesis of the product, the product α-hydroxyl β-nitroamide compound is an important intermediate in organic synthesis. The traditional Henry reaction is carried out under base catalysis, while the asymmetric catalyzed Henry reaction requires more complex reaction conditions. Generally speaking, under the condition of an organic solvent, metal / ligand complexes, chiral urea or thiourea, etc. As a catalyst, the configuration control of the product is realized. Organic reactions u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C231/24C07C235/38C07C235/16
CPCC07C231/12C07C231/24C07C235/38C07C235/16
Inventor 刘洪鑫陆文婷卢范蕴陈文品吴超飞
Owner INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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