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A kind of synthetic method of new florfenicol

A technology of florfenicol and synthetic method, which is applied in the field of florfenicol synthesis, can solve the problems of low total yield, long route, high waste water treatment cost, etc., and achieve the goal of saving treatment cost, simple reaction steps and reduced cost Effect

Active Publication Date: 2018-01-23
WEIFANG DAYOU BIOLOGICAL CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this route include: 1. A large amount of copper sulfate wastewater is produced during the preparation of copper salt, which seriously pollutes the environment and the cost of wastewater treatment is high; 2. Only half of the required configuration intermediate is obtained by splitting and separating a single isomer, although Transformation of obsolete configurations is currently possible through epimerization / hydrolysis chemistry, but with a correspondingly large increase in reaction steps and costs
This route has the disadvantages that the enzyme catalyst is not easy to obtain in the synthetic method, the route is long, and the total yield is low.

Method used

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  • A kind of synthetic method of new florfenicol
  • A kind of synthetic method of new florfenicol
  • A kind of synthetic method of new florfenicol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of (1R,2S)-3-fluoro-1-(4-(thymphenyl)benzene)-2-nitropropane-1-ol (IV)

[0031] Step 1 Preparation of catalytic solution: 3Å molecular sieve, tetrahydro-salen ligand (Ia) (82 mg, 0.2 mmol), (CuOTf) 2 .C 6 h 5 CH 3 (10 mg, 0.02 mmol) was added into dichloromethane (8 mL) to prepare a catalytic solution; the addition amount of the tetrahydro-salen ligand (Ia) was 10 mol of the addition amount of thiamphenicol benzaldehyde (II) %; the CuOTf) 2 .C 6 h 5 CH 3 The amount of added accounted for 1 mol% of the added amount of thiamphenicol benzaldehyde (II).

[0032] Step 2 Asymmetric Henry reaction: add fluoronitroethane (III) (2.1 g, 0.022 mol) to the prepared catalytic solution, stir at room temperature for 10 minutes, add p-thiamphenicol benzaldehyde (II) (3.7 g, 0.02 mol), heated to 30°C and stirred for 24 hours to carry out catalytic reaction.

[0033] Step 3 Collection: The material after the catalytic reaction was distilled under reduced p...

Embodiment 2

[0035] Example 2 Preparation of (1R,2S)-3-fluoro-1-(4-(thymphenyl)benzene)-2-nitropropan-1-ol (IV)

[0036] Step 1 Preparation of catalytic solution: 3Å molecular sieve, tetrahydro-salen ligand (Ib) (93 mg, 0.2 mmol), (CuOTf) 2 .C 6 h 5 CH 3 (10 mg, 0.02 mmol) were sequentially added into tetrahydrofuran (8 mL) to obtain a catalytic solution; the addition amount of the tetrahydro-salen ligand (Ia) was 10 mol% of the addition amount of thiamphenicol benzaldehyde (II) ; the CuOTf) 2 .C 6 h 5 CH 3 The added amount accounted for 1 mol% of the added amount of thiamphenicol benzaldehyde (II)

[0037] Step 2 Asymmetric Henry reaction: Add fluoronitroethane III (2.1 g, 0.022 mol) to the catalytic solution, stir at room temperature for 10 minutes, add p-thiamphenicol benzaldehyde II (3.7 g, 0.02 mol), heat Stir the reaction at 25 degrees for 24 hours, and the reaction is complete.

[0038] Step 3 Collection: Distill the mixed material after the catalytic reaction under reduce...

Embodiment 3

[0040] Example 3 Preparation of (1R,2S)-3-fluoro-1-(4-(thymphenyl)benzene)-2-nitropropan-1-ol (IV)

[0041] Step 1 Preparation of catalytic solution: 3Å molecular sieve, tetrahydro-salen ligand (Ic) (104 mg, 0.2 mmol), (CuOTf) 2 .C 6 h 5 CH 3 (10 mg, 0.02 mmol) were sequentially added to toluene (8 mL) to prepare a catalytic solution; the addition amount of the tetrahydro-salen ligand (Ia) was 10 mol% of the addition amount of thiamphenicol benzaldehyde (II) ; the CuOTf) 2 .C 6 h 5 CH 3 The amount of added accounted for 1 mol% of the added amount of thiamphenicol benzaldehyde (II).

[0042]Step 2 asymmetric Henry reaction: Add fluoronitroethane III (2.1 g, 0.022 mol) to the catalytic solution, stir at room temperature for 10 minutes, add p-thiamphenicol benzaldehyde II (3.7 g, 0.02 mol), heat Stir the reaction at 35°C for 24 hours, and the reaction is complete.

[0043] Step 3 Collection: The material after the catalytic reaction was distilled under reduced pressure,...

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PUM

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Abstract

The invention provides a synthesis method of florfenicol (I). The method is characterized by comprising the step of asymmetric Henry reaction: carrying out asymmetric Henry reaction on p-methylsulfuryl benzaldehyde (II) and fluoronitroethane (III) in a catalytic liquid to generate (1R,2S)-3-fluoro-1-(4-(methylsulfuryl)phenyl)-2-nitropropane-1-ol (IV). The florfenicol synthesis process does not increase the burden to the environment, and can save the pollutant treatment cost. In the florfenicol synthesis process, the reaction step is simple, thereby greatly lowering the cost. In the florfenicol synthesis process, the used catalyst is accessible, and the yield is higher.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular, the invention relates to a new synthesis method of florfenicol. Background technique [0002] Florfenicol is a β-aminoalcohol animal-specific antibiotic developed by the American Schering-Plough Company in 1979 on the basis of thiamphenicol. Compared with thiamphenicol, it has better antibacterial activity and safety , effectiveness and drug resistance, no aplastic anemia, teratogenic, carcinogenic and mutagenic effects. At present, it has been widely used in aquaculture and animal husbandry to prevent and treat bacterial diseases such as fish, pigs and cattle. [0003] At present, the industrial production of florfenicol is mainly through the reaction of p-thiamphenicol benzaldehyde with glycine and copper sulfate to prepare copper salt, and then undergo esterification to obtain racemic p-thiamphenicol phenylserine ethyl ester, which is then resolved by t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/04C07C317/32
CPCC07C315/04C07C317/32C07C317/14
Inventor 冯树海李峰耿洪军宋晓峰李维纳李文远
Owner WEIFANG DAYOU BIOLOGICAL CHEM CO LTD
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