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Preparation method of beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having optical activity

A technology of trifluoromethyl thiophene vinyl and thiophene vinyl, applied in the field of organic synthesis, can solve problems such as compound difficulties, and achieve the effects of short reaction time, high yield and optical purity, and remarkable technological progress

Inactive Publication Date: 2018-09-14
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of the present invention solves the technical problem of difficulty in synthesizing β-trifluoromethyl-β-thienyl-β-amino acid ester compounds containing tetrasubstituted carbon chiral centers in the prior art

Method used

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  • Preparation method of beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having optical activity
  • Preparation method of beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having optical activity
  • Preparation method of beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having optical activity

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Experimental program
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Embodiment 1

[0022] Under the protection of nitrogen, add unsaturated imine to the reaction tube (92.7mg, 0.3mmol), zinc powder (30mg, 0.45mmol), ethyl bromoacetate (62μL, 0.45mmol) and 3ml of anhydrous tetrahydrofuran, heated to 60 degrees and stirred, and the reaction was completed for three hours. Add 5 mL of saturated ammonium chloride aqueous solution, separate the layers, extract with ethyl acetate, and dry over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 78.6 mg, 66% yield. [α] D 27 -211.4029 (c=1.00, CHCl 3 ); FT-IR (KBr, cm -1 ):ν3254, 2981, 2961, 1724, 1644, 1372, 1172, 1079, 1031, 962, 855, 701; 1 H NMR (400MHz, CDCl 3 )δ7.24-7.28 (m, 1H), 7.10 (d, J = 3.3Hz, 1H), 7.01 (dd, J = 12.4, 8.8Hz, 2H), 6.13 (dd, J = 30.0, 16.3Hz, 1H ), 6.04(s, 1H), 4.21(q, J=7.1Hz, 2H), 3.01(dd, J=42.4, 15.3Hz, 2H), 1.26-1.31(m, 12H); 13 C NMR (101MHz, CDCl3) δ170.16(s), 140.17(s), 129.12(s), 128.01(s), ...

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Abstract

The invention discloses a preparation method of beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having optical activity. According to the preparation method, alpha-haloacetate and zinc powder are subjected to an in situ reaction to produce an organometallic zinc reagent, the organometallic zinc reagent and optically pure trifluoromethylthiophene vinyl t-butylsulfenyl ketimine are subjected to a three-component one-pot selectively Reformatsky addition reaction, and then the beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds which have a high yield, excellent diastereoselectivity and tetrasubstituted carbon chiral centers and can be easily converted and derivatized are synthesized. Raw materials required by the preparation method are cheap andeasy to obtain, the synthesis method is simple in operation, the reaction time is short, the yield and optical purity of products are high, and the method has a good application prospect and is a universal novel method for synthesizing the beta-trifluoromethyl-beta-thiophene vinyl-beta-amino acid ester compounds having the tetrasubstituted carbon chiral centers.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing fluorine-containing pharmaceutical and pesticide intermediates, in particular to an optically active β-trifluoromethyl-β-thienyl-β-amino acid Preparation method of ester compound. Background technique [0002] Chiral fluorine-containing β-amino acid compounds and their derivatives are widely used in the fields of biology, medicine, and pesticides. In recent years, their synthesis has attracted widespread attention from chemists and pharmacologists ((a) Qiu, X.L.; Qing, F. L. Eur. J. Org. Chem. 2011, 3261; (b) Mikami, K.; Fustero, S.; Sánchez-Roselló, M.; J.L.; Soloshonok, V.; Sorochinsky, A. Synthesis 2011, 3045; (c) J.-L.; Simón-Fuentes, A.; Fustero, S. Curr. Org. Chem. 2010, 14, 928; (d) Lin, D.; Wang, J.; Liu, H. Chin. J. Org. Chem.2013, 33, 2098; (e) Qiu, X.L.; Meng, W.D.; Qing, F.L. Tetrahedron 2004, 60, 6711; (f) Tarui, A.; ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/38
CPCC07D333/38
Inventor 刘振江彭莹莹杨志强马银昊胡晓钧
Owner SHANGHAI INST OF TECH