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Preparation method of D-threonine

A technology of threonine and copper threonine, which is applied in the field of preparation of D-threonine, can solve the problems of low DL-threonine yield, low total yield and high cost, and achieves a simple synthetic route and easy manual operation. The effect of high sexual content and low production cost

Active Publication Date: 2015-04-15
CHENGDU BAISHIXING SCI & TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has the following disadvantages: in order to remove the DL-allothreonine isomer, the yield of DL-threonine obtained by repeated crystallization of the threonine copper complex is low; the obtained DL-threonine must be further treated with enzyme Only by resolution can a single D-threonine be obtained, the utilization rate of the intermediate is only 50%, the total yield is low, the cost is high, it is not suitable for industrial production, and the chiral content does not meet the quality requirements of chiral compounds, so the method's App is restricted

Method used

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  • Preparation method of D-threonine
  • Preparation method of D-threonine

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Effect test

Embodiment 1

[0025] Embodiment 1: the preparation method of D-threonine, it comprises the following steps:

[0026] S1. Synthesis:

[0027] A. Dissolve glycine with a purity of 97% in 2mol / L sodium hydroxide solution, heat up to 65°C, react at a constant temperature for 6h, cool to room temperature, centrifuge, and dry to obtain copper glycine; wherein, glycine: hydroxide Sodium: the mass ratio of copper sulfate pentahydrate is 1:5:1.4;

[0028] B. Dissolve copper glycinate in water, add S-2-(diphenylhydroxymethyl)-tetrahydropyrrole, cool to 5°C, add acetaldehyde dropwise, react for 20 hours, D-threonine copper salt precipitates, separate solid Material, clean solid matter with 70% ethanol, remove lotion, get D-threonine copper salt; Wherein, copper glycinate: water: D-proline derivative: the mass ratio of acetaldehyde is 0.9:6:0.1: 1;

[0029] S2. Desalination: Dissolve D-threonine copper salt obtained in step S1 in 8% ammonia water, use hydrogen-type 732 cationic ammonia-type resin to...

Embodiment 2

[0031] Embodiment 2: the preparation method of D-threonine, it comprises the following steps:

[0032] S1. Synthesis:

[0033] A. Dissolve glycine with a purity of 98% in 2mol / L sodium hydroxide solution, heat up to 75°C, react at a constant temperature for 8h, cool to room temperature, centrifuge, and dry to obtain copper glycine; wherein, glycine: hydroxide Sodium: the mass ratio of copper sulfate pentahydrate is 1.05:6:1.6;

[0034] B. Dissolve copper glycinate in water, add N-triphenylmethyl-(L)-proline, cool to 10°C, add acetaldehyde dropwise, react for 28 hours, D-threonine copper salt precipitates, and separate solid matter , clean the solid matter with 80% ethanol, remove the lotion, and get D-threonine copper salt; wherein, copper glycinate: water: D-proline derivative: the mass ratio of acetaldehyde is 1:7:0.15:1.5 ;

[0035] S2. Desalination: Dissolve D-threonine copper salt obtained in step S1 in 12% ammonia water, use hydrogen-type 732 cationic ammonia-type res...

Embodiment 3

[0037] Embodiment 3: the preparation method of D-threonine, it comprises the following steps:

[0038] S1. Synthesis:

[0039] A. Dissolve glycine with a purity of 98.5% in 2mol / L sodium hydroxide solution, heat up to 70°C, react at a constant temperature for 7h, cool to room temperature, centrifuge, and dry to obtain copper glycine; wherein, glycine: hydroxide Sodium: the mass ratio of copper sulfate pentahydrate is 1.02:5.5:1.5;

[0040] B. Dissolve copper glycinate in water, add N-triphenylmethyl-(L)-proline, cool to 8°C, add acetaldehyde dropwise, react for 25 hours, D-threonine copper salt precipitates, and separates solid matter , clean solid matter with 76% ethanol, remove lotion, get D-threonine copper salt; Wherein, copper glycinate: water: D-proline derivative: the mass ratio of acetaldehyde is 0.95:6.8:0.12:1.3 ;

[0041] S2. Desalination: Dissolve D-threonine copper salt obtained in step S1 in 10% ammonia water, use hydrogen-type 732 cationic ammonia-type resin to...

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Abstract

The invention discloses a preparation method of D-threonine and belongs to the technical field of amino acid synthesis. The preparation method of the D-threonine specifically comprises the following steps: S1, synthesizing, namely dissolving copper glycine in water, adding D-proline derivatives, cooling to 5-10 DEG C, dropwise adding acetaldehyde, reacting for 20-28 hours, separating out the D-threonine copper salt out, separating a solid substance, washing the solid substance with 70-80% ethyl alcohol, and removing a washing liquor to obtain the D-threonine copper salt; S2, desalting, namely dissolving the D-threonine copper salt obtained in the step S1 in 8-12% ammonia water, removing copper and concentrating to obtain a D-threonine concentrated solution; S3, refining, namely decolorizing and crystallizing the D-threonine concentrated solution to prepare the D-threonine. By adopting the preparation method of D-threonine, a novel method for synthesis of the D-threonine is provided. The preparation method of D-threonine is simple in synthetic route, low in production cost, convenient to operate and high in yield. The prepared D-threonine is high in content of chirality and applicable to large-scale production in factories.

Description

technical field [0001] The invention relates to the technical field of amino acid synthesis, in particular to a preparation method of D-threonine. Background technique [0002] D-threonine (formula Ⅰ) alias D-2-amino-3-hydroxybutyric acid, the molecular formula is C 4 h 9 NO 3 , Molecular weight 119.12, white crystal or crystalline powder, easy to use in water, insoluble in ethanol, ether, chloroform, sweet taste. D-threonine is the optical isomer of natural amino acid L-threonine, and it is an important unnatural amino acid. It is mainly used in the fields of chiral drugs, chiral additives, chiral auxiliary agents, etc., and is used as a chiral source for chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is mainly used in the production of new spectrum antibiotics, D-threoninol, and threonine protective agents in the synthesis of peptides. . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/22C07C227/32
Inventor 王刚
Owner CHENGDU BAISHIXING SCI & TECH IND
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