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Linear polystyrene-supported (4S)-oxazolidine-2-benzimine as well as preparation method and application thereof

A technology of linear polystyrene and oxazolidine, which is applied to the preparation of carboxylic acid amide, organic chemical methods, chemical instruments and methods, etc., can solve the problems of difficult recycling and reuse, and achieve easy on-line detection, high yield, high The effect of stereoselectivity

Inactive Publication Date: 2012-06-27
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chiral oxazolidine-2-phenylimine is a new type of chiral auxiliary reagent, which induces asymmetric alkylation reaction, shows good asymmetric induction effect, and has good chemical yield, but the chiral auxiliary After the reagent induces an asymmetric reaction, it is difficult to recover and reuse

Method used

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  • Linear polystyrene-supported (4S)-oxazolidine-2-benzimine as well as preparation method and application thereof
  • Linear polystyrene-supported (4S)-oxazolidine-2-benzimine as well as preparation method and application thereof
  • Linear polystyrene-supported (4S)-oxazolidine-2-benzimine as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-12

[0035] Example 1-12: Preparation method of linear polystyrene supported (4S)-oxazolidine-2-phenylimine.

[0036]

Embodiment 1

[0038] N-tert-butoxycarbonyl-L-tyrosine ethyl ester (5.0 g, 16.17 mmol) was dissolved in N, N-dimethylformamide (50 mL), and a catalytic amount of 18-crown-6 and anhydrous potassium carbonate ( 6.69g, 48.51mmol), add p-vinylbenzyl chloride (3.42mL, 24.26mmol) dropwise in N,N-dimethylformamide (15mL) solution dropwise at 2 drops / second, and after the dropwise addition, at 20°C Under reaction 48h. After the solvent was distilled off under reduced pressure, ethyl acetate (100 mL) was added, washed with saturated brine (3×10 mL), dried over anhydrous magnesium sulfate, and the solvent was removed with ethyl acetate and petroleum ether (1:3, volume ratio) Recrystallization gave a white solid, the product (2S)-3-[4'-(p-vinylbenzyloxy)phenyl]-2-(N-tert-butoxycarbonyl)alanine ethyl ester (5.73g, 83.3 %). m.p.76.6-77.8°C; [α] D 20 =+0.9 (c 0.09, THF); IR (NaCl): υ3377, 2978, 1716cm -1 ; 1 HNMR (CDCl 3 , 600MHz): δ7.42 (2H, d, J = 7.8Hz, ArH), 7.37 (2H, d, J = 7.8Hz, ArH), 7.04 (...

Embodiment 2

[0040] N-tert-butoxycarbonyl-L-tyrosine ethyl ester (5.0 g, 16.17 mmol) was dissolved in N, N-dimethylformamide (50 mL), and a catalytic amount of 18-crown-6 and anhydrous potassium carbonate ( 2.23g, 16.17mmol), add p-vinylbenzyl chloride (2.28mL, 16.17mmol) dropwise in N,N-dimethylformamide (15mL) solution dropwise at 2 drops / second, and after the dropwise addition, at 60°C Under reaction 12h. After distilling off the solvent under reduced pressure, add ethyl acetate (100mL) to dilute, wash with saturated brine (3×10mL), dry over anhydrous magnesium sulfate, remove the solvent and wash with ethyl acetate and petroleum ether (1:3, volume ratio ) recrystallized to obtain a white solid, the product (2S)-3-[4'-(p-vinylbenzyloxy)phenyl]-2-(N-tert-butoxycarbonyl)aminopropionic acid ethyl ester (5.79g, 84.2%). m.p.76.6-77.8°C; [α] D 20 =+0.9 (c 0.09, THF); IR (NaCl): υ3377, 2978, 1716cm -1 ; 1 H NMR (CDCl 3 , 600MHz): δ7.42 (2H, d, J = 7.8Hz, ArH), 7.37 (2H, d, J = 7.8Hz, Ar...

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Abstract

The invention relates to linear polystyrene-supported (4S)-oxazolidine-2-benzimine which has the following structural formula, wherein m:n=1:1-4, and Mw=8300-14000. In the invention, (4S)-oxazolidine-2-benzimine is supported on linear polystyrene to prepare the linear polystyrene-supported (4S)-oxazolidine-2-benzimine as a chiral auxiliary reagent to induce asymmetric reaction into homogeneous reaction, and the reaction is rapid and convenient for on-line detection. The chiral auxiliary reagent not only reserves the high yield and the high stereoselectivity of the asymmetric reaction induced by the oxazolidine-2-benzimine as the chiral auxiliary reagent to obtain a chiral compound with high optical purity, bus also realize the recycling of the (4S)-oxazolidine-2-benzimine. The synthesizedchiral compound with high optical purity is used as the precursor, the intermediate and the final product of medicines, agricultural chemicals, spices and functional materials.

Description

technical field [0001] The invention relates to a chiral auxiliary reagent linear polystyrene supported (4S)-oxazolidine-2-phenylimine and a preparation method and application thereof. Background technique [0002] Since Merrifiled used cross-linked polystyrene as an insoluble polymer carrier to support the synthesis of peptides in 1963, solid-phase organic synthesis has been widely used in the synthesis of peptides, oligosaccharides, low-level nucleotides, and small molecule compound libraries. . However, solid-phase organic synthesis uses insoluble cross-linked polystyrene as a carrier, and the heterogeneous reaction takes a long time; it is difficult to optimize the reaction conditions by using the classic liquid-phase organic synthesis reaction conditions, and the reaction speed and method are difficult to predict; Conventional analytical methods such as TLC, HPLC, IR, and NMR cannot be used to detect the reaction process, separation purity, and product structure. Only ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F212/08C08F212/32C07D263/28C07B53/00C07C233/11C07C231/02
Inventor 卢翠芬陈祖兴夏德新胡富强杨桂春
Owner HUBEI UNIV