Chiral tetrahydroimidazolidine compound with CnFmH2n+1-m structure unit and synthesis method thereof

A technology of tetrahydroimidazolidine and structural units, which is applied in the field of chiral tetrahydroimidazolidine compounds and their synthesis, can solve problems such as discomfort and difficulty in preparing chiral diamines, and achieve good corresponding selectivity and fast catalytic reaction speed , the effect of high yield

Inactive Publication Date: 2013-03-13
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chiral tetrahydroimidazolidine compounds are mainly synthesized by the condensation reaction of chiral 1,2-diamine and aldehyde, but this method is not suitable for the synthesis of n f m h 2n+1-m The chiral tetrahydroimidazolidine compound of the structural unit, because it has C n f m h 2n+1-m It is difficult to prepare the corresponding chiral diamines of chiral tetrahydroimidazolidine compounds as structural units

Method used

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  • Chiral tetrahydroimidazolidine compound with CnFmH2n+1-m structure unit and synthesis method thereof
  • Chiral tetrahydroimidazolidine compound with CnFmH2n+1-m structure unit and synthesis method thereof
  • Chiral tetrahydroimidazolidine compound with CnFmH2n+1-m structure unit and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] preparation of

[0034] Add 0.007mmol Cu(CH 3 EN) 4 BF 4 with 0.0077mmol(S,R p )-PPF-OMe, under the protection of nitrogen, add 1mL ether, stir at room temperature for 1 hour, then add 0.35mmol 2-(4-chlorobenzylideneamino)methyl acetate, 0.035mmol Triethylamine, 0.23mmol 2,2,2-trifluoromethyl methylene anisidine, stirred for 1-2 hours, evaporated the solvent, and the product was subjected to silica gel column chromatography (petroleum ether / ethyl acetate: 10 / 1 ~5 / 1), the yield was 95%, the enantioselective excess of the product was 97%, HPLC (Chiralcel AD-H, i-propanol / hexane=10 / 90, flow rate 1.0mL / min, λ=220nm) ;t r =9.49 and 11.47min.)[α] 25 D =-44.2(c 1.0, CHCl 3 ); 1 H NMR (CDCl 3,TMS,300MHz)7.50-7.47(m,2H),7.36-7.34(m,2H),6.78-6.75(m,2H),6.68-6.66(m,2H),5.40(s,1H),4.63- 4.61(m,1H),4.32(s,1H),3.79(s,3H),3.72(s,3H),2.66(brs,1H), 13 C NMR (CDCl 3 ,TMS,100MHz)170.41,153.98,139.50,137.47,134.65,129.15,128.12,125.77(q,J=281.0Hz),117.21,114.55,81.18,65.55(q...

Embodiment 2

[0036] preparation of

[0037] Add 0.007mmol Cu(CH 3 EN) 4 BF 4 with 0.0077mmol(S,R p )-PPF-OMe, under the protection of nitrogen, add 1mL ether, stir at room temperature for 1 hour, then add 0.35mmol 2-(3-chlorobenzylideneamino)methyl acetate, 0.035mmol Triethylamine, 0.23mmol2,2,2-trifluoromethylmethyleneanisidine, after stirring for 1-2 hours, evaporated the solvent, and the product was subjected to silica gel column chromatography (petroleum ether / ethyl acetate: 10 / 1~ 5 / 1) obtained, the yield was 85%, the enantioselective excess of the product was 94%, HPLC Chiralcel AS-H, i-propanol / hexane=10 / 90, flow rate 1.0mL / min, λ=220nm); t r =7.81 and 11.19min.[α] 25 D =-42.0(c 0.3, CHCl 3 ); 1 H NMR (CDCl 3 ,TMS,300MHz)7.54(s,1H),7.44-7.42(m,1H),7.32-7.27(m,2H),6.79-6.67(m,4H),5.40(s,1H),4.64-4.57( m,1H),4.31(s,1H),3.78(s,3H),3.72(s,3H),2.69(brs,1H), 13 C NMR (CDCl 3 ,TMS,100MHz)170.42,154.07,141.13,139.52,134.80,130.31,129.14,126.94,125.74(q,J=280.0Hz),124.84,117.30,...

Embodiment 3

[0039] preparation of

[0040] Add 0.007mmol Cu(CH 3 EN) 4 BF 4 with 0.0077mmol(S,R p )-PPF-OMe, under the protection of nitrogen, add 1mL ether, stir at room temperature for 1 hour, then add 0.35mmol 2-(2-chlorobenzylideneamino)methyl acetate, 0.035mmol Triethylamine, 0.23mmol 2,2,2-trifluoromethyl methylene anisidine, stirred for 1-2 hours, evaporated the solvent, and the product was subjected to silica gel column chromatography (petroleum ether / ethyl acetate: 10 / 1 ~5 / 1), the yield is 80%, the enantioselective excess of the product is 92%, HPLC (Chiralcel AS-H, i-propanol / hexane=10 / 90, flow rate 1.0mL / min, λ=220nm) ;t r =7.85 and 8.47min.[α] 25 D =+15.1(c 1.4, CHCl 3 ); 1 H NMR (CDCl 3 ,TMS,300MHz)7.62-7.60(m,1H),7.45-7.42(m,1H),7.29-7.26(m,2H),6.78-6.75(m,2H),6.64-6.61(m,2H), 5.85(s,1H),4.62-4.59(m,1H),4.32(s,1H),3.79(s,3H),3.71(s,3H), 13 C NMR (CDCl 3 ,TMS,100MHz)170.57,153.82,139.45,136.29,133.47,129.98,129.87,127.75,127.41,125.74(q,J=281.0Hz),116.62,114.56...

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Abstract

The invention discloses a chiral tetrahydroimidazolidine compound with a CnFmH2n+1-m structure unit and a synthesis method thereof. The synthesis method comprises the following steps of: in an organic solvent and under the protection of inert gas, by taking fluorine-containing alkylmethyleneanisidine and methylamino acid-derived imine as raw materials and taking a complex of metal lewis acid/chiral ligand as a catalyst, adding carbonate or organic base, sufficiently reacting at (-40)-30 DEG C, steaming to remove solvent, and performing column chromatography to obtain the target compound. The compound can be used as an active ingredient of an antibacterial agent.

Description

technical field [0001] The invention relates to a chiral tetrahydroimidazolidine compound and a synthesis method thereof, in particular to a compound with C n f m h 2n+1-m A chiral tetrahydroimidazolidine compound of a structural unit and a synthesis method thereof. Background technique [0002] Chiral tetrahydroimidazolidines are an important class of compounds, mainly used in some drugs and biologically active compounds ((a) S.Vibha, M.S.Y.Khan Eur.J.Med.Chem.2001,36,651-658(b )R.S.Carleton, D.M.Melissa, J.S.Thomas, B.Donna, N.Robert, F.-M.Janet, M.S.Robert.Biochemistry 1998,37,13893-13901.), the tetrahydroimidazole ring is also an organic small molecule catalyst core structure. Compounds containing trifluoromethyl also play an important role in pesticides and medical treatment. In the process of modern new drug design and development, it is often considered to introduce one or more fluorine atoms into the drug molecule to affect the activity of the drug molecule. Ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/02C07D405/04C07D409/04C07D233/28A01N43/50A01P3/00
Inventor 王春江李清华陶海燕
Owner WUHAN UNIV
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