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A kind of preparation method of florfenicol reduction product intermediate

The technology of an intermediate, florfenicol, is applied in the field of preparation of a florfenicol reductant intermediate, can solve the problems of low overall yield, long synthesis steps, large amount of waste water and the like, and achieves improved economy, simple operation, The effect of efficient use

Active Publication Date: 2020-11-20
京山瑞生制药有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0007] Prepare the Florfenicol intermediate (1R, 2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane-1,3-diol using the above route, and the amount of waste water produced by copper salts exists in the production Large, and due to the split method, its atom utilization rate is only half, the overall yield is low, the synthesis steps are longer, and the operation is more complicated

Method used

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  • A kind of preparation method of florfenicol reduction product intermediate
  • A kind of preparation method of florfenicol reduction product intermediate
  • A kind of preparation method of florfenicol reduction product intermediate

Examples

Experimental program
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Embodiment 1

[0038] 1. Synthesis of copper salt complex Cu(OTf)2 / L:

[0039] In a 100ml three-necked flask, dissolve pyridine-2-carbaldehyde (2.14g, 0.02mol) in ethanol, add cis-1,2-cyclohexanediamine (2.28g, 0.02mol), and heat to 80°C for reaction 2 hours, spin-dried and purified to obtain the intermediate (1S, 2R, E)-N1-(pyridin-2-ylmethylene)cyclohexane-1,2-diamine (1.98g, y=49%), Dissolve the intermediate in ethanol (20ml), add 2,5-dihydroxyterephthalaldehyde (0.8g, 4.87mmol), heat to 40°C for 6 hours, cool down to room temperature after the reaction is complete, add hydroboration Sodium (0.93g, 24.35mmol), stirred for 4 hours, added ammonium chloride and ethyl acetate, extracted and separated, the organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain a crude product, which was separated by column chromatography to obtain the ligand L (1.06 g, 40%). The synthesized ligand L was dissolved in methanol, a toluene solution of Cu(OTf)2 (3.9 mmol) was added, and a...

Embodiment 2

[0046] 1. Synthesis of copper salt complex Cu(OTf)2 / L:

[0047] In a 100ml three-necked flask, dissolve pyridine-2-carbaldehyde (2.14g, 0.02mol) in ethanol, add cis-1,2-cyclohexanediamine (2.28g, 0.02mol), and heat to 80°C for reaction 2 hours, spin-dried and purified to obtain the intermediate (1S, 2R, E)-N1-(pyridin-2-ylmethylene)cyclohexane-1,2-diamine (1.98g, y=49%), Then dissolve the intermediate in ethanol (20ml), add 2,5-dihydroxyterephthalaldehyde (0.8g, 4.87mmol), heat to 40°C for 6 hours, cool down to room temperature after the reaction is complete, add hydroboration Sodium (0.93g, 24.35mmol), stirred for 4 hours, added ammonium chloride and ethyl acetate, extracted and separated, the organic phase was dried over anhydrous sodium sulfate, spin-dried to obtain a crude product, and separated by column chromatography to obtain the ligand L (1.06 g, 40%). The synthesized ligand L was dissolved in methanol, a toluene solution of Cu(OTf)2 (3.9 mmol) was added, and after ...

Embodiment 3

[0054] 1. Synthesis of copper salt complex Cu(OTf)2 / L:

[0055] In a 100ml three-necked flask, dissolve pyridine-2-carbaldehyde (2.14g, 0.02mol) in ethanol, add cis-1,2-cyclohexanediamine (2.28g, 0.02mol), and heat to 80°C for reaction 2 hours, spin-dried and purified to obtain the intermediate (1S, 2R, E)-N1-(pyridin-2-ylmethylene)cyclohexane-1,2-diamine (1.98g, y=49%), Then dissolve the intermediate in ethanol (20ml), add 2,5-dihydroxyterephthalaldehyde (0.8g, 4.87mmol), heat to 40°C for 6 hours, cool down to room temperature after the reaction is complete, add hydroboration Sodium (0.93g, 24.35mmol), stirred for 4 hours, added ammonium chloride and ethyl acetate, extracted and separated, the organic phase was dried over anhydrous sodium sulfate, spin-dried to obtain a crude product, and separated by column chromatography to obtain the ligand L (1.06 g, 40%). The synthesized ligand L was dissolved in methanol, a toluene solution of Cu(OTf)2 (3.9 mmol) was added, and after ...

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Abstract

The invention discloses a preparing method of a florfenicol reduzate intermediate. The florfenicol intermediate ((1R,2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane-1,3-diol) is prepared through asymmetric addition reaction and sodium methyl mercaptide / oxidizing reaction with p-chlorobenzaldehyde as the initial raw material. The method is simple in whole path, simple in reaction operation, good in chiral control and broad in application prospect. The two-step reaction is greatly simplified compared with the four-step reaction of the traditional process, operation is simpler, the high-efficiency utilization of a substrate is realized, and compared with a traditional chiral separation process with the atom utilization rate less than 50%, the economical efficiency of the process is greatly improved.

Description

technical field [0001] The invention belongs to the technical field of veterinary drug synthesis, and in particular relates to a preparation method of a florfenicol reduced product intermediate. Background technique [0002] Florfenicol (Florfenicol) Chinese name: fluprofen; Florfenicol is a commonly used veterinary antibiotic at present. It has a broad antibacterial spectrum, strong antibacterial effect, low minimum inhibitory concentration (MIC), and its antibacterial effect is 15-20 times that of chloramphenicol and thiamphenicol. At present, China is the main producer and exporter of veterinary antimicrobial Florfenicol. According to statistics, in 2015, the export of florfenicol in my country reached 2199 tons, and with the rectification of food safety in recent years, the amount used in the international animal protection market has continued to expand. [0003] The structural formula of the Florfenicol intermediate (1R, 2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/32B01J31/02
CPCB01J31/0271B01J2231/34C07B2200/07C07C213/00C07C315/00C07C317/32C07C215/36
Inventor 张治国钟旭辉周国朝徐相雨
Owner 京山瑞生制药有限公司
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