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Novel method for synthesizing 2-amino-2-thiazoline-4-carboxylic acid

A synthesis method and thiazoline technology are applied in the synthesis field of fermentation precursor 2-amino-2-thiazoline-4-carboxylic acid, and can solve the problems of low product quality, low yield, complicated steps and the like, and achieve yield High, improve product quality, the effect of simple method

Active Publication Date: 2011-02-09
山东祥维斯生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Although the above several methods can make 2-amino-2-thiazoline-4-carboxylic acid, the steps are complicated, the yield is lower, and the quality of the product prepared is lower

Method used

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  • Novel method for synthesizing 2-amino-2-thiazoline-4-carboxylic acid
  • Novel method for synthesizing 2-amino-2-thiazoline-4-carboxylic acid
  • Novel method for synthesizing 2-amino-2-thiazoline-4-carboxylic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 80g (0.5mol) of 3-chloro-alanine hydrochloride and 300ml water into a 500ml three-necked flask and stir to dissolve, then add 41g (0.5mol) of sodium thiocyanate solid into the reaction flask, and continue stirring at room temperature Mix for 15 minutes, adjust the pH to 8.0-9.0 with sodium carbonate, heat in a water bath to 60°C, and continue to use sodium carbonate to maintain the pH, consume a total of 29-30g of sodium carbonate, and react at 60°C for 3 hours to obtain 3-chloro-2-thiourea A pale yellow reaction solution of propionic acid. Concentrated hydrochloric acid was added dropwise to the reaction solution with a constant pressure dropping funnel to adjust the pH to 6.0-7.5. Then raise the temperature to 90°C, keep the reaction at 90°C, and carry out the ring-closing reaction for 2 hours. After the reaction is completed, when the temperature is lowered to 40°C, in order to speed up the crystallization, a small amount of crystal seeds or friction wall can be ...

Embodiment 2

[0026] Add 52.6g (0.5mol) of 3-hydroxy-alanine hydrochloride and 300mol water into a 500ml three-necked flask and stir to dissolve, then add 41g (0.5mol) of sodium thiocyanate solid into the reaction flask, and stir and mix at room temperature for 15min , adjust the pH to 8.5-9.0 with about 29g of sodium carbonate, raise the temperature to 65°C, and keep the temperature to continue the reaction for 2.8h to obtain a light yellow reaction solution of 3-hydroxy-2-thioureidopropionic acid, add dropwise to the reaction solution Concentrated hydrochloric acid, adjust the pH to 7.0-7.5, then raise the temperature to 100°C, keep warm for 1.8h for closed-loop reaction. After the reaction is complete, cool down to 38°C, add seed crystals to induce crystallization, then continue to cool down to 5-10°C, keep for 32 minutes, then filter, wash the product with 100ml of cold water to obtain 2-amino-2-thiazoline-4-carboxylic acid, Vacuum-dried at 50-60°C to obtain 69.5 g of the finished produ...

Embodiment 3

[0028] Add 84g (0.5mol) of 3-bromo-alanine hydrochloride and 300ml water into a 500ml three-necked flask and stir to dissolve, add 41g (0.5mol) of sodium thiocyanate solid, stir and mix at room temperature for 10min, adjust the pH with sodium carbonate To 8.0-8.5, the temperature was raised to 55°C, and the pH was maintained, and the reaction was carried out at 55°C for 3.2h. A reaction solution of 3-bromo-2-thioureidopropionic acid was obtained. Concentrated hydrochloric acid was added dropwise to the reaction solution to adjust the pH to 6.0-6.5. The temperature was raised to 85°C, and the ring-closing reaction was maintained for 2.2 hours. After the reaction is completed, when the temperature is lowered to 45°C, crystallization is induced on the wall of the friction vessel, and the temperature is further lowered to 4-6°C, kept for 35 minutes, filtered, and the product is washed with 100ml of cold water to obtain 2-amino-2-thiazoline-4-carboxylic acid, Vacuum-dried at 50-6...

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Abstract

The invention discloses a method for preparing 2-amino-2-thiazoline-4-carboxylic acid. 3-X-lactamine hydrochloride and sodium sulfocyanate react in medium water to generate 3-X-2-thioureido monoprop, and the 3-X-2-thioureido monoprop has a ring-closure reaction to prepare the 2-amino-2-thiazoline-4-carboxylic acid. The method is simple, convenient to operate, has high yield coefficient which is more than 95 percent, and greatly enhances the quality of products.

Description

technical field [0001] The invention relates to a synthesis method of 2-amino-2-thiazoline-4-carboxylic acid (abbreviated as ATC), a fermentation precursor of L-cysteine. Background technique [0002] 2-Amino-2-thiazoline-4-carboxylic acid, English name 2-amino-2-thiazoline-4-carboxylic acid, the structural formula is as follows: [0003] [0004] 2-Amino-2-thiazoline-4-carboxylic acid is a racemate, hereinafter referred to as (dl-ATC)ATC. As a precursor for the synthesis of cysteine, ATC is widely used in the field of medicine. Cysteine ​​was originally made from animal hair as a raw material through acid, alkali, and enzyme hydrolysis, and then after separation and purification, it was reduced and crystallized to form cysteine, but it has the disadvantages of long synthetic route and cumbersome operation, and the animal There are few sources of hair, and the source of raw materials is greatly restricted. [0005] The development of an easy-to-operate and low-cost rou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/18
Inventor 刘世普陈国民马兴群
Owner 山东祥维斯生物科技股份有限公司
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