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Producing process for threonine benzyl ester oxalate

A technology of threonine benzyl oxalate and threonine benzyl ester, which is applied in the field of medicine and chemical industry

Inactive Publication Date: 2004-09-01
四川三高生化股份有限公司
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

There is no literature report on the synthesis technology and process of threonine benzyl oxalate

Method used

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Examples

Experimental program
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Effect test

Embodiment Construction

[0014] ①. Pump 380kg carbon tetrachloride (CCl) into the 1000L glass-lined kettle 4 ), 120kg benzyl alcohol (BzlOH), drop into 36kg L-threonine (L-Thr) under stirring, 68kg p-toluenesulfonic acid. Hydrate (TosOH.H 2 (2), reflux divides water, divides in 10h (from reflux to start counting), divides 11kg of water, stops heating;

[0015] ②. Concentrate the reaction solution in "①" with carbon tetrachloride (CCl 4 ), a viscous liquid with threonine benzyl p-toluenesulfonate (L-Thr.OBzl.TosOH) as the main component;

[0016] 3. Add 15kg ethanol (EtOH) and 75kg ethyl acetate (AcOEt) in the viscous liquid of last step gained, slowly add 55kg sodium carbonate (NaOEt) after stirring and dissolving 2 CO 3 ) powder, neutralize and remove p-toluenesulfonic acid (TosOH) in L-threonine benzyl ester p-toluenesulfonate (L-Thr.OBzl.TosOH) to obtain L-threonine benzyl ester (Thr.OBzl) A mixture of organic solution and sodium p-toluenesulfonate (TosONa);

[0017] 4. shake off and remove th...

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Abstract

The invention relates to the production method of a threonine benzyl ester oxalates belonging to the field of pharmaceutical and chemical industry, wherein threonine of different forms (L-, DL-, D-Thr) are reacted with phenylcarbinol under the catalysts of p-toluenesulfonic acid, the threonine benzyl ester p-toluenesulfonic acid (Thr.Obzl.TosOH) is further synthesized directly in on step through the mode of azeotropic dehydration, then the threonine benzyl ester p-toluenesulfonic acid salts are suspended in the organic solvent to neutralize p-toluenesulfonic acid directly through inorganic bases, water scrubbing the organic facies, charging oxalic acid directly in organic solvent to obtain the threonine benzyl ester oxalate crude product of the corresponding formation, the crude product is then purified by alcohols to obtain the threonine benzyl ester oxalates end product.

Description

technical field [0001] The invention relates to a production method of threonine benzyl oxalate. It belongs to the technical field of medicine and chemical industry. Background technique [0002] Threonine benzyl oxalate [Thr.OBzl.n(COOH) 2 ] can be used as an intermediate in the synthesis of threonine derivatives or as a chiral source for the synthesis of a large number of organic compounds or drugs. Because threonine has carboxyl and hydroxyl functional groups, in the process of synthesizing esters, especially benzyl esters, it is necessary to increase the esterification rate and avoid side reactions caused by hydroxyl groups, including etherification and dehydration. At the same time, from the perspective of production, post-treatment must be reduced process or avoid decomposition during postprocessing. Directly using oxalic acid as a catalyst for the esterification of threonine and benzyl alcohol, the reaction rate is too low. If other acids are used to catalyze the ...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C229/22
Inventor 张国林刘林叶丁袁汉张仁友杨朝雪王佰国钟永东张晓斌林鸿赵平张伦
Owner 四川三高生化股份有限公司
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