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New method for preparing L-tertiary leucine

A technology of tert-leucine and a new method, which is applied in the field of preparing L-tert-leucine, can solve problems such as high operation requirements, hidden safety hazards, and environmental pollution, and achieve the effects of reducing environmental pollution, improving safety, and being environmentally friendly

Active Publication Date: 2014-12-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional Strecker reaction uses sodium cyanide or potassium cyanide as a cyanide reagent. Because the reagent is a highly toxic reagent, there are not only great safety hazards in production, high operation requirements, but also serious environmental pollution.

Method used

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  • New method for preparing L-tertiary leucine

Examples

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Effect test

Embodiment 1

[0042] The synthesis of the aminonitrile compound of embodiment 1 magnesium diiodide catalysis

[0043] Pivalaldehyde (8.6g, 0.1mol) and L-phenylglycol (15.1g, 0.11mol) were added to a dry 100mL single-necked flask, and MgI was added under the protection of nitrogen. 2 (10mmol), after stirring for 10min, add TMSCN (11.9g, 0.12mol), stir the reaction at room temperature, TLC detects the reaction process, and adds Na after the end of the reaction. 2 S 2 o 3 The reaction was quenched with aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain an aminonitrile compound (20.88 g, 0.09 mol) with a yield of 90%.

Embodiment 2

[0044] Embodiment 2 Synthesis of the aminonitrile compound catalyzed by magnesium dibromide

[0045] Add pivalaldehyde (10.32g, 0.12mol) and L-phenylglycol (18.08g, 0.132mol) into a dry 100mL single-necked flask, under the protection of nitrogen, add magnesium dibromide (12mmol), and stir for 10min Then add TMSCN (14.286g, 0.144mol), stir the reaction at room temperature, TLC detects the reaction progress, after the reaction finishes, add Na 2 S 2 o 3 The reaction was quenched with aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain aminonitrile compound (24.22 g, 0.104 mol) with a yield of 87%.

Embodiment 3

[0046] Example 3 Synthesis of aminonitrile compounds catalyzed by magnesium dichloride

[0047]Pivalaldehyde (12.9g, 0.15mol) and L-phenylene glycol (22.6g, 0.165mol) were added to a dry 100mL single-necked flask, under the protection of nitrogen, magnesium dichloride (1.43g, 15mmol) was added, and stirred After 10min, TMSCN (17.8g, 0.18mol) was added, the reaction was stirred at room temperature, the reaction progress was detected by TLC, and Na 2 S 2 o 3 The reaction was quenched with aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain an aminonitrile compound (28.54 g, 0.12 mol) with a yield of 82%.

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Abstract

The invention discloses a new method for preparing L-tertiary leucine. The new method comprises the following steps: 1, performing asymmetric cyanosilylation reaction on pivalaldehyde, L-phenylglycinol and trimethylsilyl cyanide in the presence of a catalyst A, and carrying out posttreatment to obtain a compound I; 2, hydrolyzing the compound I under acidic condition, and carrying out posttreatment to obtain a compound II; 3, performing catalytic hydrogenation reaction on the compound II to obtain L-tertiary leucine, wherein the catalyst A is magnesium diiodide, magnesium dibromide, magnesium dichloride, magnesium perchlorate or magnesium trifluoromethanesulfonate. The stereochemistry of the L-tertiary leucine can be constructed with high selectivity under solvent-free condition by adopting a magnesium catalyzed three-component one-pot asymmetric cyanosilylation reaction through cheap and easily available organic raw materials.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a new method for preparing L-tert-leucine. Background technique [0002] Unnatural chiral α-amino acids are widely used in many types of marketed drugs due to their important physiological activities and structural diversity. Many chiral drugs contain chiral α-amino acid skeleton, which has become a hot spot in modern drug research. Therefore, the efficient and high stereoselective synthesis of unnatural chiral α-amino acids has become one of the important contents of current research. [0003] L-tert-leucine is a non-natural chiral α-amino acid. Due to the large steric hindrance of the tert-butyl group, the derivatives of tert-leucine are used as templates to induce asymmetry in asymmetric synthesis. With the development of asymmetric synthesis, the application of tert-leucine is also very extensive. And because of the large tert-butyl chain and its hydrophobicity, it can wel...

Claims

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Application Information

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IPC IPC(8): C07C227/30C07C229/08
Inventor 张兴贤卢勇平竺越施建杰陈嘉丽
Owner ZHEJIANG UNIV OF TECH
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