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Synthetic method of furazolidone metabolite AOZ

A technology of oxazolone and reaction, which is applied in the field of chemical synthesis, can solve the problems of difficult separation and purification and low yield, and achieve the effect of easy separation and purification and increased yield

Active Publication Date: 2020-06-19
INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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AI Technical Summary

Problems solved by technology

[0003] The productive rate of the synthetic product of the method for synthesizing 3-amino-2-oxazolone (AOZ) at present is low, is not easy to separate and purify

Method used

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  • Synthetic method of furazolidone metabolite AOZ
  • Synthetic method of furazolidone metabolite AOZ
  • Synthetic method of furazolidone metabolite AOZ

Examples

Experimental program
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Embodiment 1

[0028] Embodiment 1, synthetic 3-amino-2-oxazolone (AOZ)

[0029]

[0030] Step 1: Place ethylene glycol (5g, 1.0 equivalents) in an ice-water bath, add PBr dropwise 3 (2.6 mL, 0.377 equivalents) for 5 min, then warmed to room temperature, and finally heated to the reflux temperature of ethylene glycol, and reacted for 3 hours. After the reaction was completed, the solvent was distilled to obtain 6.0 g of the reaction intermediate product 2-bromoethanol (60% yield). For the reaction flow chart, see figure 1 .

[0031] Step 2: tert-butylcarbazole (NH 2 NH 2 Boc) (2.0 equivalents, 2.11g) and sodium hydroxide (1.3 equivalents, 416mg) were dissolved in a round bottom flask containing ethanol (20ml), while 2-bromoethanol (1.0 equivalents, 1.0g) was dissolved in ethanol (5ml ) was added dropwise in the reaction solution, after reacting at room temperature for 4h, all the reaction solution was evaporated to dryness, and the column chromatography purification conditions were: ...

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Abstract

The invention discloses a preparation method of 3-amino-2-oxazolidinone (AOZ). The method comprises the following steps: 1) carrying out a reaction on ethylene glycol and PBr3 to obtain 2-bromoethanol; 2) in the presence of an alkali, carrying out a reaction on NH2NH2Boc and 2-bromoethanol to obtain Boc protected 2-hydrazinoethanol; 3) in the presence of an alkali, carrying out a reaction on Boc protected 2-hydrazinoethanol and diethyl carbonate to obtain Boc protected 3-amino-2-oxazolidinone; and 4) performing deprotection on the Boc group in the Boc protected 3-amino-2-oxazolidinone to obtain 3-amino-2-oxazolidinone. According to the method, the yield of AOZ in the synthesis process is obviously increased, and separation and purification are facilitated.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing furazolidone metabolite AOZ. Background technique [0002] Furazolidone (furazolidone) is a hydrazone formed by 5-nitrofurfural and 3-amino-2-oxazolidinedione, commonly known as furazolidone, which belongs to nitrofuran drugs. It is a synthetic spectrum antibacterial drug that began to be used in the late 1940s. It has certain antibacterial and anti-inflammatory effects, and is widely used in the prevention and treatment of livestock and poultry, aquatic animal diseases, sterilization and disinfection of aquatic animal breeding environments, and prevention and treatment of intestinal infections in livestock and poultry. Many studies have proved that furazolidone has strong side effects (Wang Qingwei, Liu Xueying, Li Ping, Cheng Jianfeng. Adverse reactions and prevention of furazolidone [J]. Chinese Journal of Hospital Pharmacy. 2000 (03): 55...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/26
CPCC07D263/26Y02P20/55
Inventor 王敏王彤彤全灿周剑杨梦瑞刘权辉
Owner INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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