Method for preparing optical pure p-hydroxy phenyl glycine by separation method

A p-hydroxyphenylglycine and optical technology, which is applied in the field of preparing optically pure p-hydroxyphenylglycine by a splitting method, can solve the problems of increasing the requirement of a splitting agent, increasing the cost of the splitting agent, etc., and achieves the effect of reducing the production cost.

Inactive Publication Date: 2010-08-04
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the resolution reagents used in the above method are all optically pure, and three of them need to be used at the same time. Compared with the traditional classic resolution using an optically pure resolution reagent, the requirements for the resolution agent are increased, and at the same time, the resolution is improved. On the basis of the separation efficiency, the cost of the resolving agent is also greatly increased

Method used

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  • Method for preparing optical pure p-hydroxy phenyl glycine by separation method

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Effect test

Embodiment 1

[0030] (1) Add 167g (1mol) of racemized p-hydroxyphenylglycine to 450mL of ethanol / water solution (volume ratio: 1:1), heat reflux to 276.46g (1mol) combined cyclic phosphoric acid resolving agent until the solution is clear, and stir for 1h. After cooling to 50°C, crystals were precipitated, filtered, washed the filter cake with 56 mL of ice water, and dried to obtain 218.4 g of filter cake with a melting point of 230°C-232°C.

[0031] The main resolving agent in the combined cyclic phosphoric acid resolving agent is (-)-CP2, the auxiliary resolving agent is (±)-CP3, and the molar ratio of the two is 99:1.

[0032] (2) Dissolve the above filter cake in 50 mL of 36% hydrochloric acid, stir at room temperature for 4 hours, precipitate a large amount of solids and filter, recover the cyclic phosphoric acid resolving agent, adjust the pH=5.4 of the filtrate with NaOH solution, filter, wash with 15 mL of ice water, and dry. 81.33 g of D-(-)-p-hydroxyphenylglycine was obtained, and...

Embodiment 2

[0036](1) In 400mL isopropanol / water solution (volume ratio is 1:1), add 167g (1mol) of racemized p-hydroxyphenylglycine, 276.41g (1mol) combined cyclic phosphoric acid resolving agent, heat and reflux until the solution is clear , stirred for 1 h, cooled to 50°C, crystals precipitated, filtered, washed the filter cake with 53mL of ice water, and dried to obtain 214.6g of filter cake with a melting point of 231°C-233°C.

[0037] The main resolving agent in the combined cyclic phosphoric acid resolving agent is (-)-CP2, and the auxiliary resolving agent is (-)-CP3, and the molar ratio of the two is 98:2.

[0038] (2) Dissolve the above filter cake in 45mL of phosphoric acid, stir at room temperature for 4h, precipitate a large amount of solid and filter. The cyclic phosphoric acid resolving agent was recovered, and the filtrate was adjusted to pH=5.4 with KOH solution, filtered, washed with 14 mL of ice water, and dried to obtain 79.78 g of D-(-)-p-hydroxyphenylglycine with a y...

Embodiment 3

[0042] (1) In 450mL of methanol / water solution (volume ratio is 1:1), add 167g (1mol) of racemized p-hydroxyphenylglycine, 272.02g (1mol) of combined cyclic phosphoric acid resolving agent, heat and reflux until the solution is clear, and stir After cooling to 50°C for 1h, crystals were precipitated, filtered, washed the filter cake with 50mL of ice water, and dried to obtain 214g of filter cake with a melting point of 226°C-258°C.

[0043] The main resolving agent in the combined cyclic phosphoric acid resolving agent is (-)-CP3, the auxiliary resolving agent is (±)-CP2, and the molar ratio of the two is 99.5:0.5.

[0044] (2) Dissolve the above filter cake in 48mL of 18% dilute sulfuric acid, stir at room temperature for 4h, precipitate a large amount of solid and filter. Reclaim cyclic phosphoric acid resolving agent, filtrate uses Na 2 CO 3 The solution was adjusted to pH=5.4, filtered, washed with 11 mL of ice water, and dried to obtain 79.87 g of D-(-)-p-hydroxyphenylg...

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Abstract

The invention discloses a method for preparing optical pure p-hydroxy phenyl glycine by a separation method, and belongs to the field of separating racemic compounds. In the method, laevo-rotation cycle phosphoric acid serving a main separating agent and cycle phosphoric acid serving as an auxiliary separating agent are used together to separate DL-p-Hydroxyphenylglycine, and particularly, the DL-p-Hydroxyphenylglycine and the combined cycle phosphoric acid separating agent are reacted in a water-containing organic solvent, the reaction solution is heated and refluxed until the reaction solution is clear, the reaction solution is stirred and cooled to precipitate crystals, the reaction solution is filterer and washed, the obtained filter cakes are treated to form the D-(-)-p-hydroxy phenyl glycine, and the filtrate and the water-washing solution are treated to obtain the L-(+)-p-hydroxy phenyl glycine. The method has the advantages of high yield, high optical purity, high separation efficiency, easy and convenient operation, and the like.

Description

technical field [0001] The invention relates to a method for preparing optically pure p-hydroxyphenylglycine by a resolution method, in particular to a method for preparing its L-(+)- and D-(-)-p-hydroxyphenylglycine by resolving racemic p-hydroxyphenylglycine. Construct method. Background technique [0002] Photoactive p-hydroxyphenylglycine has important uses, and can be used in the synthesis of broad-spectrum antibiotics, and in the auxiliary treatment of ischemic heart disease, heart failure, diabetes and other diseases. [0003] The preparation method of photoactive p-hydroxyphenylglycine includes biological enzyme method, chemical resolution method and induced crystallization method. [0004] At present, photoactive p-hydroxyphenylglycine is mainly produced by induced crystallization of racemic p-hydroxyphenylglycine with o-toluenesulfonic acid or p-toluenesulfonate. This method is low in cost but too low in efficiency. The extraction process after preparation of pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/34
Inventor 孙凤霞张旭于奕锋
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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