Synthesis method of alpha-ketoamide compound

A synthesis method and technology for ester compounds, which are applied in the fields of amide synthesis and organic synthesis, can solve the problems of complicated reaction operation, harsh reaction conditions and high production cost, achieve simple synthesis steps, high product yield and purity, and avoid post-production problems. processing effect

Active Publication Date: 2020-11-27
WUYI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although many methods have been found to synthesize, in the process of preparing α-ketoamides under these reaction conditions, it is inevitable to use organic solvents and additives.
Among them, the most common synthesis method of α-ketoamide compounds usually uses metal catalysis, mainly using heavy metals such as palladium, copper, and gold as catalysts; the reaction conditions of this type of reaction are harsh, the reaction operation is relatively complicated, and there are cases where the reaction is incomplete appear; therefore, it will cause a lot of pollution to the environment, and its production cost is relatively high

Method used

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  • Synthesis method of alpha-ketoamide compound
  • Synthesis method of alpha-ketoamide compound
  • Synthesis method of alpha-ketoamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Add 0.5 mmol of phenyl isocyanate compound and 0.6 mmol of benzoylformic acid to a 25 ml screw-top test tube successively, stir and react at 60°C for 6 hours, and cool to room temperature after the reaction to obtain the crude product , the crude product was purified by column chromatography to obtain the product 3aa with a yield of 92% and a purity of 99%.

[0063] The synthetic route is:

[0064]

[0065] The resulting product 3aa is a pale yellow solid, and its hydrogen spectrum and carbon spectrum are as follows figure 1 with figure 2 As shown, the structural characterization data are as follows:

[0066] 1 H NMR (500MHz, CDCl 3 )δ8.97(s,1H),8.42(d,J=7.6Hz,2H),7.73-7.64(m,3H),7.52(t,J=7.7Hz,2H),7.41(t,J=7.9 Hz,2H),7.21(t,J=7.4Hz,1H);

[0067] 13 C NMR (126MHz, CDCl 3 ) δ 187.5, 158.9, 136.6, 134.7, 133.1, 131.5, 129.3, 128.6, 125.4, 119.9.

Embodiment 2

[0069] Add 0.5 mmol of 4-chlorophenylisocyanate and 0.6 mmol of benzoylformic acid to a 25 ml screw-top test tube in turn, stir and react at 60°C for 6 hours, and cool to room temperature after the reaction to obtain The crude product was purified by column chromatography to obtain product 3ad with a yield of 86% and a purity of 99%.

[0070] The synthetic route is:

[0071]

[0072] The resulting product 3ab is a light yellow solid, and its hydrogen spectrum and carbon spectrum are as follows image 3 with Figure 4 As shown, the structural characterization data are as follows:

[0073] 1 H NMR (500MHz, CDCl 3 )δ9.00(s,1H),8.40(dd,J=8.3,1.1Hz,2H),7.70-7.63(m,3H),7.51(dd,J=10.9,4.8Hz,2H),7.40-7.33 (m,2H);

[0074] 13 C NMR (126MHz, CDCl 3 ) δ 187.1, 158.8, 135.2, 134.8, 132.9, 131.5, 130.4, 129.3, 128.7.

Embodiment 3

[0076] Add 0.5 mmol of 4-iodophenylisocyanate and 0.6 mmol of benzoylformic acid to a 25 ml screw-top test tube in turn, stir and react at 60°C for 8 hours, and cool to room temperature after the reaction to obtain The crude product was purified by column chromatography to obtain the product 3ac with a yield of 79% and a purity of 98%.

[0077] The synthetic route is:

[0078]

[0079] The resulting product 3ac is a light yellow solid, and its hydrogen spectrum and carbon spectrum are as follows Figure 5 with Image 6 As shown, the structural characterization data are as follows:

[0080] 1 H NMR (500MHz, CDCl 3 )δ8.99 (s, 1H), 8.39 (dt, J = 8.5, 1.4Hz, 2H), 7.72-7.63 (m, 3H), 7.49 (ddt, J = 9.7, 4.8, 2.2Hz, 4H);

[0081] 13 C NMR (126MHz, CDCl 3 ) δ 187.0, 158.9, 138.2, 136.4, 134.8, 132.9, 131.5, 128.6, 121.7, 88.9.

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Abstract

The invention discloses a synthesis method of an alpha-ketoamide compound. The preparation method comprises the following steps of: taking an isocyanate compound as shown in a formula I and a benzoylformic acid compound as shown in a formula II as raw materials, and carrying out heating reaction to obtain the alpha-ketoamide compound as shown in a formula III, wherein the reaction formula is described in the specification, and in the formula, R1 and R2 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl or aromatic heteroradical. The synthesis method has the advantages that the synthesis steps are simple, the operation is safe, the compatibility of the synthesis method with functional groups is good,, the alpha-ketoamide compound with very high additional value is obtained, the yield can reach 92%, the purity is 99%, the experiment cost or the production cost is greatly reduced, industrial synthesis is easy, and another new synthesis thought is provided for constructing more alpha-ketoamide drugs.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, relates to the field of amide synthesis, in particular to a synthesis method of α-ketoamide compounds. Background technique [0002] α-Ketoamide and its derivatives are the key skeleton structures of many biologically active compounds, such as immunosuppressants FKBP12 and FK506, cytosolic phosphatase A2 inhibitors, estrogen and androgen receptors, etc. α-Ketoamide compounds not only have great potential in medicine, but because they are a class of compounds with a bifunctional structure and have multiple active centers, they are useful conversion precursors for functional groups in chemistry, pesticides, and chemical engineering. , textiles and many other fields have a wide range of applications. It is precisely because of the importance and universality of α-ketoamide and its derivatives that it is extremely important to develop a simple, green and efficient method for synthesizing α...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/78C07C235/74C07C231/10C07D307/54
CPCC07C231/10C07D307/54C07C2601/14C07C235/78C07C235/74
Inventor 朱忠智梁柏辉黄俊杰范成谦陈修文梁京文
Owner WUYI UNIV
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