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Stable isotope labeled furaltadone metabolite and synthesis method thereof

A technology of stable isotope and synthesis method, which is applied in the field of stable isotope-labeled furotadone metabolites and their synthesis, can solve the problems of restricting the development of the veterinary drug residue detection industry, expensive isotope-labeled raw materials, difficult production process, etc., and achieves good economic The effect of high stability, high atomic utilization rate and high use value

Inactive Publication Date: 2020-04-21
SHANGHAI ANPEL SCI INSTR
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the synthesis method of AMOZ has been reported in the literature (Org.Lett., 2012, 14, 4874-4877; Anal.Methods, 2014, 6, 2306-2313; CN103420934A), but because the price of isotope-labeled raw materials is more expensive, the cost is higher , The production process is difficult to realize, how to ensure that the isotope atoms will not fall off during the production process, product purification and other technical difficulties. The synthesis method of stable isotope-labeled AMOZ has not been reported, which seriously restricts the development of the veterinary drug residue detection industry in the field of food safety in my country.

Method used

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  • Stable isotope labeled furaltadone metabolite and synthesis method thereof
  • Stable isotope labeled furaltadone metabolite and synthesis method thereof
  • Stable isotope labeled furaltadone metabolite and synthesis method thereof

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preparation example Construction

[0020] The synthetic method of the stable isotope-labeled furaltadone metabolite provided by the invention comprises the following steps:

[0021] S1: reacting stable isotope-labeled epichlorohydrin with morpholine to prepare stable isotope-labeled morpholino-based propylene oxide; the molecular structure of the stable isotope-labeled epichlorohydrin is:

[0022]

[0023] The molecular structure of the morpholino propylene oxide labeled with the stable isotope is:

[0024]

[0025] S2: react the stable isotope-labeled morpholino propylene oxide with hydrazine hydrate to obtain stable isotope-labeled 1-hydrazino 3-morpholine-2 propanol; the stable isotope-labeled 1-hydrazino 3- The molecular structure of morpholine-2 propanol is:

[0026]

[0027] S3: Under alkaline conditions, react the stable isotope-labeled 1-hydrazino 3-morpholine-2 propanol with a substituted formate to obtain a stable isotope-labeled furaltadone metabolite; the stable isotope The molecular stru...

Embodiment 1

[0030] The molecular structure of the stable isotope-labeled furaltadone metabolite is as follows:

[0031]

[0032] Prepared by the following synthetic steps:

[0033] S1. Add 3.7g morpholine and 5.0g tert-butanol to the reaction vessel, place it in an ice-salt bath, add 4.0g epichlorohydrin-D5 dropwise through a constant pressure dropping funnel, and control the temperature during the dropping process at 0 ~27°C, the dropping time is 30~40min. After the dropping is completed, keep the reaction at 20~30°C for 18 hours. 25g 20wt% tetrahydrofuran solution of potassium tert-butoxide, the dropwise addition process controls the temperature at 0-15°C, after the dropwise addition is completed, the temperature is kept at 10-15°C for 2 hours, and column chromatography is used to obtain morpholino propylene oxide-D5 ;

[0034]S2. Add 5.0g morpholino propylene oxide-D5, 40mL ethanol, 6.5g 80% hydrazine hydrate to the reaction vessel, keep it warm at 80-90°C for 3 hours, and distill...

Embodiment 2

[0039] The synthesis process of stable isotope-labeled furaltadone metabolites is as follows:

[0040] S1. Add 4.0g morpholine and 6.0g tert-butanol to the reaction vessel, place it in an ice-salt bath, add 4.0g epichlorohydrin-D5 drop by drop through a constant pressure dropping funnel, and control the temperature during the dropping process at 0 ~27°C, the dropping time is 30~40min. After the dropwise addition is completed, keep the reaction at 20~30°C for 20 hours, then place the reaction vessel in an ice-salt bath, and add dropwise through a constant pressure dropping funnel. 30g of 20wt% tetrahydrofuran solution of potassium tert-butoxide, the dropwise addition process controls the temperature at 0-15°C, after the dropwise addition is completed, it is incubated at a temperature of 10-15°C for 2.5 hours, and column chromatography obtains morpholino propylene oxide- D5;

[0041] S2. Add 5.0g morpholino propylene oxide-D5, 50mL ethanol, 6.0g 85% hydrazine hydrate to the rea...

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Abstract

The invention discloses a stable-isotope-labeled furaltadone metabolite and a synthesis method thereof. The method includes reacting stable-isotope-labeled epichlorohydrin which is used as a stable isotope labeling source and morpholine to obtain stable-isotope-labeled morpholinyl epoxypropane; then reacting with hydrazine hydrate to obtain stable-isotope-labeled 1-hydrazino-3-morpholinyl-2-propanol; and finally reacting with substituted formate under an alkaline condition to obtain the stable-isotope-labeled furaltadone metabolite. The invention provides the synthesis method of the stable-isotope-labeled furaltadone metabolite for the first time; the stable isotope labeling raw material is cheap and easy to obtain, the synthesis process is simple, the product is easy to separate and purify, and the chemical purity and isotope abundance of the obtained product both reach 99% or above, meeting the requirement for serving as a standard reagent for quantitatively detecting furaltadone metabolite. The metabolite has high application value and good economy performance.

Description

technical field [0001] The invention relates to the field of isotope labeling, in particular to a stable isotope-labeled furaltadone metabolite and a synthesis method thereof. Background technique [0002] Nitrofuran drugs are important antimicrobial drugs, mainly including nitrofurazone, nitrofurantoin, furaltadone and furazolidone. Nitrofuran drugs have certain antibacterial effects on both Gram-positive and Gram-negative bacteria, including Salmonella, Shigella, Escherichia coli, Klebsiella pneumoniae, Enterobacter, and Staphylococcus aureus , Enterococcus faecalis, Streptococcus pyogenes, Vibrio cholerae, Campylobacter and Bacteroides, etc., also have inhibitory effects on Trichomonas and Giardia at a certain concentration. It is mainly used for bacillary dysentery, enteritis, and cholera caused by sensitive bacteria, and can also be used for typhoid, paratyphoid, giardiasis, and trichomoniasis. It can also be used for urinary system infections caused by sensitive bact...

Claims

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Application Information

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IPC IPC(8): C07D263/26
CPCC07D263/26C07B2200/05
Inventor 郭会陈武炼
Owner SHANGHAI ANPEL SCI INSTR
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