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Alpha-fluoroalkyl-alpha-amino acid compound containing tetrasubstituted carbon chiral center and preparation method thereof

An amino acid and fluorine-containing alkyl technology, which is applied in the field of organic synthesis, can solve the problems of inability to obtain α-fluoroalkyl-α-amino acid compounds, etc., and achieves high yield, cheap and easily available raw materials, and good application prospects. Effect

Inactive Publication Date: 2015-11-04
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the above-mentioned technical problems in the prior art, the present invention provides an α-fluoroalkyl-α-amino acid compound containing a tetrasubstituted carbon chiral center and a preparation method thereof. The α-fluoroalkyl-α-amino acid compound with a sex center and its preparation method solve the technical problem that the α-fluoroalkyl-α-amino acid compound with a tetrasubstituted carbon chiral center cannot be obtained in the prior art

Method used

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  • Alpha-fluoroalkyl-alpha-amino acid compound containing tetrasubstituted carbon chiral center and preparation method thereof
  • Alpha-fluoroalkyl-alpha-amino acid compound containing tetrasubstituted carbon chiral center and preparation method thereof
  • Alpha-fluoroalkyl-alpha-amino acid compound containing tetrasubstituted carbon chiral center and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Dissolve fluorine-containing alkyl unsaturated ketone 1, chiral sulfenamide, and tetraethoxytitanium in an organic solvent, heat to reflux for 24 hours, quench the reaction, filter, separate and extract, dry, and column chromatography to obtain product 2 .

[0033] Further, the product 2 was dissolved in an organic solvent, under the protection of an inert gas, and an organolithium reagent was added under the condition of -40°C. After the reaction was completed, the reaction was quenched, liquid separation, extraction, drying, and column chromatography were performed to obtain the product 3.

[0034] Further, the product 3 was dissolved in an organic solvent, an aqueous solution of hydrogen chloride was added at room temperature, stirred at room temperature for 2 hours, and the solvent was spin-dried to obtain product 4.

[0035] Further, dissolve the product 4 in an organic solvent, add triethylamine, potassium carbonate, and benzoyl chloride, heat overnight for reacti...

Embodiment 2

[0051] Add 1g to the reaction bottle 666 mg 3g Ti(OEt) 4 , 45ml tetrahydrofuran, reflux at 80°C for 24 hours, cool to room temperature, add 30ml saturated sodium chloride aqueous solution, filter, wash the filter cake with ethyl acetate, combine the filtrate, separate liquid, extract with ethyl acetate, combine the organic phase, anhydrous Dried over sodium sulfate, filtered to remove the desiccant, spin-dried the solvent, and performed flash column chromatography (PE:EA=15:1) to obtain the product 1.3 g, 86% yield.

[0052] mp:55-56℃; [α] D 20 -985.76 (c=0.70, CHCl 3 ); FT-IR (KBr, cm -1 ):ν2964,2932,1617,1583,1451,1197,1144,1126,1079,977,762,698; 1 H NMR (400MHz, CDCl 3 ):δ8.00(d,J=16.8Hz,1H),7.44-7.47(m,2H),7.27-7.30(m,3H),7.23(d,J=16.8Hz,1H),1.25(s, 9H); 19 F NMR (376MHz, CDCl 3 ):δ-66.26(s,3F); 13 C NMR (CDCl 3): δ158.66(q, J=32.9Hz), 143.77(q, J=2.7Hz), 134.65, 130.86, 128.89, 128.35, 118.88(q, J=282.4Hz), 115.09, 60.58, 22.89.

[0053] Under argon prote...

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Abstract

Belonging to the field of organic synthesis, the invention provides an alpha-fluoroalkyl-alpha-amino acid compound containing a tetrasubstituted carbon chiral center, and also discloses a preparation method of the compound. The method utilizes cheap and easily available fluoroalkyl-containing unsaturated ketone and chiral prosthetic group sulfinamide as the starting raw material, and by means of preparation of alpha, beta-unsaturated fluoroalkyl sulfenyl ketoimine, selective addition of an organic metallic reagent and chiral alpha, beta-unsaturated imine, removal of chiral prosthetic group, protection of amino group, and finally double-bond simple oxidation in order, the alpha-fluoroalkyl-alpha-amino acid compound containing the tetrasubstituted carbon chiral center can be obtained by entiomeric purity. The method provided by the invention has the advantages of cheap and easily available raw materials, simple operation of the synthesis method, good selectivity, high yield, and reaction with universal applicability, is a universal method for synthesis of the alpha-fluoroalkyl-alpha-amino acid compound containing the tetrasubstituted carbon chiral center, and has very good application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a fluorine-containing medicine, pesticide, chemical intermediate and its synthesis method, in particular to an α-fluoroalkyl-α-amino acid compound containing a four-substituted carbon chiral center and its preparation method. Background technique [0002] Fluorine-containing amino acids are a very important class of unnatural amino acids. Due to the strong electron-withdrawing ability, high lipophilicity and large steric hindrance of the fluorine-containing groups, the fluorine-containing amino acids show some special characteristics. physiological activity. Many fluorine-containing amino acids have been used as probes to track biochemical reactions ((a) Vocadlo, D.J.; Mayer, C.; He, S.M.; Withers, S.G. Biochemistry 2000, 39, 117-126; (b) Namchuk, M.N.; McCarter , J.D.; Becalski, A.; Andrews, T.; Withers, S.G.J.Am.Chem.Soc.2000, 122, 1270-1277.(c) Dubios, J.; Dugave, C.; M.; T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/20C07C227/18
CPCY02P20/55
Inventor 刘振江吴范宏刘朋杨志强陈世豪
Owner SHANGHAI INST OF TECH
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