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Method for synthesizing trifluoromethyl-containing oxazolone compound by one-pot method
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A technology of trifluoromethyl oxazolone and compounds, which is applied in the field of asymmetric synthesis, and can solve problems affecting yield and ee value, difficult to control, easy to deteriorate, etc.
Active Publication Date: 2021-06-04
HENAN NORMAL UNIV
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[0003] However, it is precisely because the one-pot method is a series of multi-step reactions, and there are many reactions, so it is more difficult to control. At present, the one-pot method mostly occurs in biosynthesis, and it still has great challenges in organic chemical synthesis.
[0004] α-CF 3 The asymmetric catalytic reaction that the compound directly participates in as a nucleophile is still very limited. In the face of this challenge, the applicant found that 2-trifluoromethyl-oxazol-5(2H)-one can directly participate as a nucleophile Asymmetric catalytic reaction synthesizes compounds containing trifluoromethyl oxazolones, but 2-trifluoromethyl-oxazol-5(2H)-one itself is not very stable, it is easy to deteriorate, and if it is not handled in time, it will affect the reaction Yield and ee value
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Embodiment 1
[0025]
[0026] The synthetic steps of racemic compound 3 are as follows:
Embodiment 2
[0030]
[0031]
[0032]
[0033] a Unless otherwise stated, la (0.075 mmol), Cat. (0.005 mmol), 2a (0.05 mmol), solvent (0.5 mL). b Isolated yield. c The dr value was obtained by protonspectrum analysis of the crude product. d The ee value is obtained by chiral column HPLC chiral analysis. EDCI: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, EDC: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, DCC : N,N'-dicyclohexylcarbodiimide.
[0034] In the screening process of reaction conditions, the influence of different chiral catalysts on the reaction was first investigated (entries1-10), and it was found that C10 was the best chiral catalyst. In addition, in addition to the catalysts listed in the above table, there are many catalysts used Products with different ee values can also be obtained, such as amino acid derivatives, quinines, quinidines and other alkaloid catalysts. Afterwards, the effects of different condensing agents on the reaction were ...
Embodiment 3
[0038]
[0039] Compound 1a (0.15mmol, 1.5eq), catalyst (0.01mmol, 0.1eq), DCC (0.15mmol, 1.5eq), 1mL mesitylene and compound 2b (0.1mmol, 1.0eq) were added to the reaction flask at 25 The reaction was carried out under the condition of ℃, and the reaction was monitored by thin-layer plate (TLC). After 2 hours of reaction, column chromatography (eluent: PE:EA=50:1-10:1) separated and obtained white solid 3b, 91% ee, product The rate is 90%. 1 H NMR (400MHz, CDCl 3 )δ8.07(d,J=8.2Hz,2H),7.76(d,J=8.2Hz,2H),4.21-4.06(m,2H),4.04(dd,J=10.3,3.5Hz,1H), 3.73(dd,J=18.3,10.3Hz,1H),3.57(dd,J=18.3,3.5Hz,1H),1.37(s,9H),1.28(t,J=7.1Hz,3H).
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Abstract
The invention discloses a method for synthesizing trifluoromethyl-containing oxazolone compounds by a one-pot method, and belongs to the field of organic chemistry. N-trifluoroacetyl amino acid (1) and alpha, beta-unsaturated ketone (2) are subjected to a one-pot high-stereoselectivity and high-enantioselectivity reaction under the action of a thiourea catalyst and DCC to obtain the trifluoromethyloxazolone compound (3). According to the one-pot reaction, the time can be shortened, many tedious steps are omitted, the trifluoromethyl-containing oxazolone compound is obtained, and the trifluoromethyl-containing oxazolone compound has high optical purity and high stereoselectivity.
Description
technical field [0001] The invention belongs to the technical field of asymmetric synthesis in organic chemistry, and in particular relates to a method for synthesizing compounds containing trifluoromethyl oxazolones in one pot. Background technique [0002] The one-pot method is a very promising organic synthesis method. The multi-step series reaction in the one-pot reaction can start from relatively simple and easy-to-obtain raw materials, and directly obtain molecules with complex structures without the separation of intermediates, which can save a lot of It saves a lot of cumbersome processing steps, which is obviously economically and environmentally friendly. [0003] However, it is precisely because the one-pot method is a series of multi-step reactions, and more reactions are carried out, so it is more difficult to control. At present, the one-pot method mostly occurs in biosynthesis, and it still poses great challenges in organic chemical synthesis. [0004] α-CF ...
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