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Oligopeptide-like chiral selector and preparation method thereof

A chiral selector, oligopeptide-like technology, applied in chemical instruments and methods, other chemical processes, etc., can solve problems such as improving enantioselectivity, and achieve the effects of mild synthesis conditions, easy operation, and good chiral separation ability.

Inactive Publication Date: 2012-07-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because of its flexible primary structure and secondary structure, it can be used as a good chiral selector. Chinese patent CN 102059105A has prepared a new chiral stationary phase based on oligopeptide-like chiral selector; the The chiral side chains of the oligopeptide-like chiral selectors covered by the invention patent are uniform, and the structure has strong regularity, but its enantioselectivity still has great limitations and needs to be further improved

Method used

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  • Oligopeptide-like chiral selector and preparation method thereof
  • Oligopeptide-like chiral selector and preparation method thereof
  • Oligopeptide-like chiral selector and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] preparation of

[0043] (1) Preparation

[0044] Add 11.68g (160mmol) of tert-butylamine and 8.48g (80mmol) of anhydrous sodium carbonate (or 80mmol of triethylamine) into a 250ml single-port reaction flask, and dissolve them with 50mL of acetone. The reaction solution was cooled to 0° C. under an ice-water bath, and 20 mL of an acetone solution of 18.08 g (160 mmol) of chloroacetyl chloride was slowly added dropwise with stirring. After about 1 hour, the reaction was complete, and the solvent was distilled off under reduced pressure. The residue was acidified with 2M HCl and extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 16.74 g of a white solid product with a yield of 70%. 1H NMR (CDCl3): 1.38 (s, 9H), 3.93 (s, 2H), 6.36 (s, 1H).

[0045] (2) Preparation

[0046] Weigh 14.95g (100mmol) of the product of step (1) and 12.10g (100mmol) of (S)-1-phenethylamine and dissolve it i...

Embodiment 2

[0050] preparation of

[0051] According to the method described in Example 1, t-butylamine was used as the starting amine in step (1).

[0052] intermediate Light yellow oily liquid, 1 HNMR (CDCl 3 ): δ0.92(t, 3H), 1.30-1.40(m, 2H), 1.48-1.56(m, 2H), 3.26-3.32(m, 2H), 4.03(s, 2H), 6.58(s, 1H ).

[0053] intermediate colorless oily liquid 1 HNMR (CDCl 3 ): δ0.92(t, 3H), 1.28-1.35(m, 2H), 1.37(d, 3H), 1.43-1.51(m, 2H), 1.79(s, 1H), 3.14(s, 2H), 3.20-3.26 (m.2H), 3.72 (q, 1H), 7.12 (s, 1H), 7.21-7.35 (m, 5H).

[0054] The target final product is a white solid, the total yield is 32%, [M+H] + =557.51.

Embodiment 3

[0056] preparation of

[0057] According to the method described in Example 1, diisopropylamine was used as the starting amine in step (1).

[0058] intermediate Light yellow oily liquid, 1 HNMR (CDCl 3 ): δ1.25 (d, 6H), 1.38 (d, 6H), 3.40-3.55 (m, 1H), 3.95-4.05 (m, 1H), 4.08 (s, 2H).

[0059] intermediate yellow oily liquid 1 HNMR (CDCl 3 ): δ1.07(d, 6H), 1.38(m, 9H), 1.97(s, 1H), 3.15-3.25(m, 2H), 3.38-3.52(m, 1H), 3.62-3.70(m, 1H ), 3.76 (q, 1H), 7.21-7.36 (m, 5H).

[0060] The target final product is a white solid, the total yield is 28%, [M+H] + = 585.64.

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Abstract

The invention provides an oligopeptide-like chiral selector and a preparation method thereof. The oligopeptide-like chiral selector is prepared by connecting a plurality of same or different amine compounds (HNR2R3)(chiral amine generally) by using a halogenated carboxylic acid or acylation reagent (XCO-R1-Y); and a general molecular formula of the oligopeptide-like chiral selector can be represented as [R2'R3'N(-CO-R1'-)NR2''(-CO-R1''-)NR2'''...(-CO-R1...-)NR2...R3...], wherein a connecting part R1 on a main chain as well as a substituent group R2 and a substituent group R3 on a side chain can be chiral or achiral, but at least one of the connecting part R1, the substituent group R2 and the substituent group R3 is chiral. Due to a flexible primary structure and a flexible secondary structure, the chain oligopeptide-like compound can be simply derived and then is coated or bonded onto the surface of a carrier to form an effective chiral stationary phase. The kind of chiral selector has relatively broad enantioselectivity and relatively high synthetic stability, and can be effectively used for analytical-grade or preparation-grade separation of chiral samples.

Description

【Technical field】 [0001] The invention relates to the technical field of oligopeptide-like chiral selectors, in particular to an oligopeptide-like chiral selector applicable to bonding or coating chiral stationary phases and a preparation method thereof. 【Background technique】 [0002] Chiral substances are an important class of chemical substances ubiquitous in nature. A pair of enantiomeric compounds often have the same physical and chemical properties, such as melting point, solubility, etc., but there are also great differences in some physical and chemical properties, such as optical activity, odor, and interaction with chiral substances to produce different products. In particular, many biochemical reactions closely related to organisms are related to the chirality of substances. There are sometimes significant differences in the pharmacological activity, metabolic process and toxicity of enantiomers of chiral chemical drugs in the human body. Because biological macr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30
Inventor 梁鑫淼柯燕雄吴海波苏小兵李奎永金郁
Owner EAST CHINA UNIV OF SCI & TECH