(S)-amino acid Schiff base coordination compound, preparation method and application thereof

A technology of alanine Schiff base and dimethyl butyric acid Schiff base is applied in the field of preparation of amino acid Schiff base complexes, can solve problems such as application limitation of chiral prosthetic group II, and achieves low cost and simple method , the effect of expanding the scope of application

Inactive Publication Date: 2010-06-30
上海攀祺生化技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the application of chiral prosthetic group II is greatly limited

Method used

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  • (S)-amino acid Schiff base coordination compound, preparation method and application thereof
  • (S)-amino acid Schiff base coordination compound, preparation method and application thereof
  • (S)-amino acid Schiff base coordination compound, preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0015] Dissolve 25.00 g (0.0486 mol) of compound II and 7.00 g (0.2916 mol) of sodium hydride in 75 mL of N,N-dimethylformamide, stir at room temperature for about 1 h, then add 18.37 g of isopropyl bromide (0.1458 mol), After the addition, the reaction solution was heated to 40-50°C, and stirred for about 2 hours, then an appropriate amount of distilled water was added dropwise to the reaction solution to precipitate crystals to obtain the amino acid Schiff base complex I with a yield of 71%. The measured values ​​of elemental analysis of complex I: C, 67.01%; H, 6.03%; N, 7.65%; Ni, 10.61%; O, 8.70%. Theoretical: C, 67.17%; H, 6.00%; N, 7.58%; Ni, 10.59%; O, 8.66%. Complex I with CDCl 3 NMR of the solvent ( 1 H-NMR): δ: 8.04~8.10(m, ArH, 3H), 7.32~7.50(m, ArH, 7H), 7.10~7.13(m, ArH, 1H), 6.95~7.09(m, ArH, 1H) , 6.61~6.94(m, ArH, 2H), 4.54~4.57(m, -CH=, 1H), 2.42~3.58(m, -CH2-, 2H), 2.03~3.15(m, -CH 2 -,6H), 2.06(s,-CH 3 , 3H), 1.10~1.12(d, -CH 3 , 3H), 0.92~0.96(d, -CH...

Embodiment 2

[0017] Dissolve 20.00 g of amino acid Schiff base complex I in 25 mL of methanol, then add 20 mL of 6 mol / L hydrochloric acid, and heat to reflux. After cooling, remove prolyl-2-aminobenzophenone BPB by filtration, and then use ion exchange resin to remove nickel ions to obtain (S)-2-amino-2,3-dimethylbutyric acid with a yield of 90%. (S)-2-Amino-2,3-dimethylbutanoic acid measured elemental analysis values: C, 54.87%; H, 9.91%; N, 10.71%; O, 24.51%. Theoretical: C, 54.94%; H, 9.99%; N, 10.68%; O, 24.39%. (S)-2-Amino-2,3-dimethylbutanoic acid with D 2 O is the NMR of the solvent ( 1 H-NMR): δ: 2.14~2.21 (m, -CH=, 1H), 1.49 (s, -CH 3 , 3H), 0.99~1.05(m, -CH 3 , 6H). The results showed that the synthesized product was (S)-2-amino-2,3-dimethylbutanoic acid.

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Abstract

The invention discloses an amino acid Schiff base coordination compound (S)-prolyl-2-aminobenzophenone-(S)-2-amino-2, 3-methylbutanoic acid Schiff base nickel, and a preparation method. The preparation method is characterized in that second halogenoalkane participates in the reaction to form the amino acid Schiff base coordination compound. The method prepares the target amino acid Schiff base coordination compound through the reaction of chiral auxiliary alanine Schiff base coordination compound (S)-prolyl-2-aminobenzophenone-(S)-amino acid Schiff base coordination compound and second halogenoalkane isopropyl nickel. The invention widens the application range of chiral auxiliary alanine Schiff base coordination compound (S)-prolyl-2-aminobenzophenone-(S)-amino acid Schiff base nickel, so through the method, more types of non-natural chiral amino acid can be synthetized.

Description

technical field [0001] The invention relates to an amino acid Schiff base complex, in particular to a method for preparing the amino acid Schiff base complex in which secondary halogenated hydrocarbons participate in the reaction. Background technique [0002] Amino acid Schiff base complex I(S)-prolyl-2-aminobenzophenone-(S)-2-amino-2,3-dimethylbutyric acid Schiff base nickel is a new amino acid Schiff base complexes. The complex is prepared by the reaction of chiral prosthetic group II(S)-prolyl-2-aminobenzophenone-(S)-alanine Schiff base nickel with secondary halogenated hydrocarbon isopropyl bromide , after hydrolyzing it, the alanine beta-disubstituted derivative (S)-2-amino-2,3-dimethylbutanoic acid can be prepared. The method for preparing amino acids with chiral prosthetic alanine Schiff base complex II is relatively simple, and is applicable to the synthesis of amino acids with various special structures [Y.N.Belokon ', V.I.Maleev, T.F.Savel'eva, et al, Russ.Chem ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16C07F15/04C07C227/18C07C229/08
Inventor 廖雪明包其郁郑乐和
Owner 上海攀祺生化技术有限公司
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