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Method for synthesizing AE-active ester by using water-containing 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino acetic acid

A technology of hydrous thioxime and active ester, applied in the direction of organic chemistry, etc., can solve the problems of many reaction steps, long reaction period, high operation intensity, etc., and achieve the effect of improving utilization rate, improving production efficiency and saving investment.

Active Publication Date: 2012-02-01
BEIJING UNIV OF CHEM TECH +1
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  • Abstract
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AI Technical Summary

Problems solved by technology

This production process has many disadvantages, such as many reaction steps, long reaction cycle, high operation intensity, low yield and many wastes.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Get 50g of water-containing aminothioxamic acid, put it into a 500mL crystallizer, 200g of solvent acetonitrile, heat to boiling and reflux for 0.5hr, then extract the water-containing solvent, supplement anhydrous acetonitrile, and when the moisture in the solution is reduced to less than 0.1% , cooled to 5°C, added acetonitrile to 150mL, added dichloromethane 150mL, added dibenzothiazole disulfide, triphenylphosphine, and triethylamine, stirred for 3 hours, and filtered to obtain AE-active ester. The product yield is 94.3%.

[0030]

Embodiment 2

[0031] Embodiment 2: get the water-containing aminothiaxamic acid of 50g, put into 500mL crystallizer, 300g solvent acetone, be heated to boiling reflux 1hr, then extract water-containing solvent, supplement dichloromethane, when the moisture in the solution reaches requirement, cool down to 10 ℃, add acetone and dichloromethane to 400mL, add dibenzothiazole disulfide, triphenylphosphine, and triethylamine and stir for 3 hours, then filter to obtain AE-active ester. The product yield is 93.5%.

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PUM

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Abstract

The invention discloses a method for synthesizing AE-active ester by using water-containing 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino acetic acid. The method comprises the following steps of: performing azeotropic dehydration on water-containing 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino acetic acid by using a solvent in a reaction container; and directly synthesizing the AE-active ester. The method has the advantages of reducing filtering and drying processes in the original production process, increasing the utilization rate of 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino acetic acid, saving investment and lowering the production cost of the AE-active ester along with extremely high industrial popularization value.

Description

technical field [0001] The invention relates to a method for synthesizing AE-active ester by using water-containing aminothiaxamic acid, which is suitable for the production process of antibiotic intermediates. Background technique [0002] AE-active ester, also known as 2-(2-amino-4-thiazolyl)-2-(methoxyimino) thiobenzothiazolyl acetate, English name: 2-(2-Amino-4- Thiazolyl)-2-methoxyiminoacetic, thiobenzothiazole ester, abbreviated as MAEM, CAS number: 80765-85-0, molecular formula: C13H10N3O2S3, molecular weight: 350.44, melting point at 128-130°C, off-white or light yellow needle-like crystal powder . Aminothioxamic acid, also known as 2-methoxyimino-2-(2-aminothiazole)-4-acetic acid, its English name is (Z)-2-(2 –aminothiazol-4-yl)-2-methoxyiminoacetic acid , referred to as ATMAA, CAS number 65872-41-5, molecular formula C 6 h 7 N 3 o 3 S, the molecular weight is 201.21. Anhydrous aminothioxamic acid is white or off-white powdery crystals, with a melting point o...

Claims

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Application Information

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IPC IPC(8): C07D277/74
Inventor 周志茂刘振强屈一新董永利王际东
Owner BEIJING UNIV OF CHEM TECH
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