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Chiral tartaric acids derivatives and preparation method thereof

A technology for tartaric acid and derivatives, which is applied in the field of derivatization preparation by utilizing chiral tartaric acid hydroxyl groups, can solve the problems of high toxicity and corrosiveness of trichlorotoluene, difficult industrialized production, and limited applicability, and achieves good ecological benefits, preparation The effect of low cost and various structures

Inactive Publication Date: 2008-08-13
广州市金匮贸易有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method is not widely applicable, and is easily limited by the form of the raw material - some acid chlorides are solid and difficult to add dropwise, and trichlorotoluene is very toxic and corrosive
This makes this method limited, and there are also problems such as direct addition of acid chlorides that may easily cause local temperature to be too high, making it difficult to apply to large-scale industrial production of various tartaric acid resolving agents.

Method used

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  • Chiral tartaric acids derivatives and preparation method thereof
  • Chiral tartaric acids derivatives and preparation method thereof
  • Chiral tartaric acids derivatives and preparation method thereof

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preparation example Construction

[0024] The preparation method of the above-mentioned chiral tartaric acid derivatives comprises the following steps: (1) in a solvent environment, the tartaric acid and the acid chloride are catalyzed, and after the acid chloride is added dropwise, thionyl chloride is added to the reaction system to promote the reaction to be carried out thoroughly (2) hydrolyzing the acid anhydride product obtained in step (1) to obtain chiral tartaric acid derivatives of the above formula; (3) post-processing the reaction waste liquid and recovering acid chlorides by means of acid-base intermodulation.

[0025] In the step (1), in a solvent environment, add a catalyst to the tartaric acid, and add 2-2.6 times the acid chloride of the tartaric acid dropwise to the reaction system between 90°C and 100°C, calculated by moles; Calculated in terms of moles, after the dropwise addition of the acid chloride, add 0.2-1 times the amount of thionyl chloride to the reaction system dropwise, and keep sti...

Embodiment 1

[0029] Embodiment 1: the preparation of L-dibenzoyl tartaric acid

[0030] 1) Preparation of L-dibenzoyl tartaric anhydride

[0031]Add 300ml of toluene and 100g of L-tartaric acid into a 1000ml reaction vessel (with condenser tube, tail gas absorption, thermometer, dropping funnel), stir and add a catalytic amount of zinc chloride. Stir and heat to between 90°C and 95°C, and add dropwise a toluene solution containing 216g of benzoyl chloride. Drop it at 90°C--95°C within about 3 hours. Weigh 96g of thionyl chloride and add it dropwise between 90°C and 95°C for about 3 hours. Slowly raise the temperature to 105°C--110°C, and keep the temperature constant for 2 hours. After natural stirring and cooling for 4 hours, cool down to normal temperature with cooling water. The reaction system was pumped under reduced pressure to remove excess hydrogen chloride gas. After filtration, the filter cake was soaked and washed with a small amount of ethyl acetate, dried at 60° C. for 12...

Embodiment 2

[0034] Embodiment 2: the resolution effect of L-dibenzoyl tartaric acid

[0035] Put 1000g of DL-aspartic acid-β-methyl ester in a 1000mL three-neck flask, add 200mL of water to dissolve all DL-aspartic acid-β-methyl ester, raise the temperature to 90°C, add 124g of L-DBTA, The solid dissolved immediately, and then cooled to room temperature, a large number of crystals precipitated, filtered, and dried to obtain 154 g of D-aspartic acid·L-DBTA salt, with a yield of 88.5%. Melting point: 150-152°C [α] D 20 (Methanol) = -60.4°.

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Abstract

The invention discloses a chiral tartaric acid derivative and a preparing method thereof. The chiral tartaric acid derivative is prepared by reacting acyl chloride with tartaric acid in the presence of catalyst, adding thionyl chloride so that the reaction is performed sufficiently, and hydrolyzing the obtained anhydride products. The waste liquid is treated and acyl chloride is recoveried at the same tiem by using an acid and alkali neutralization method. The chiral tartaric acid derivative of the invention has various structures, low preparation cost and simple production process, both steps for preparing the chiral tartaric acid derivative reach the yield more than 85% and purity more than 90%, so that the chiral tartaric acid derivative is suitable for industrial production. The invention also proposes the recovery scheme of the reaction waste liquid during the preparation process, thereby, the material is effectively recoveried and good ecological benefit is be obatined.

Description

technical field [0001] The invention relates to a chiral tartaric acid resolving agent capable of resolving various chiral drug intermediates and a preparation method thereof, in particular to a method for derivatizing and preparing by using a chiral tartaric acid hydroxyl group. Background technique [0002] "Chirality" is one of the essential properties of nature. Many biological macromolecules, such as proteins, polysaccharides, nucleic acids and enzymes, which are the important basis of life activities, almost all have "chirality" characteristics. There are many chiral compounds in nature, and these chiral compounds have two isomers, which are like real objects and mirror images, and are usually called enantiomers. Enantiomers are a lot like your left and right hands, they look very similar, but not identical. When a chiral compound enters a living body, its two enantiomers usually exhibit different biological activities (such as the chiral drug "reactin"). [0003] At...

Claims

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Application Information

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IPC IPC(8): C07C69/76C07C67/14C07C67/28C07B57/00
Inventor 周志真胡昱孙晓霞郭瑛姚华陈红卫
Owner 广州市金匮贸易有限公司
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