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Preparation method of florfenicol intermediate

A technology of florfenicol and intermediates, which is applied in the field of preparation of florfenicol intermediates, can solve the problems of many by-products, low yield and high atomic economic cost, and achieves reduction of by-product generation and improved yield , the effect of reducing the cost of synthesis

Active Publication Date: 2018-07-27
深圳蓝新科技有限公司
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  • Abstract
  • Description
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Problems solved by technology

[0006] The object of the present invention is to overcome the above-mentioned deficiencies of the prior art, a kind of preparation method of Florfenicol intermediate is provided, to solve the synthetic intermediate [R(R*, R*)-2-amino-1-[to- (Methylsulfonyl) phenyl] propane-1,3-diol is the technical problem that the reduction of potassium borohydride leads to relatively many by-products, low yield and relatively high atomic economic cost.

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  • Preparation method of florfenicol intermediate
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  • Preparation method of florfenicol intermediate

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preparation example Construction

[0014] The invention provides a preparation method of florfenicol intermediate. The preparation method of the florfenicol intermediate includes the following steps:

[0015] S01: Provide compound A with the following structural formula:

[0016]

[0017] S02: The compound A is subjected to an oxidation-reduction reaction in a solvent containing an acridine salt photocatalyst and a reducing agent to generate compound B of the following structural formula:

[0018]

[0019] Specifically, the compound A in the step S01 is named D-(-)-threo-[p-(methylsulfonyl)phenyl]serine ethyl ester, which can be prepared according to conventional methods.

[0020] In the light reaction in the step S02, the compound A undergoes an oxidation-reduction reaction with the reducing agent under the action of light and the catalysis of the acridine salt photocatalyst to produce the compound B as a product. The chemical reaction formula of the redox reaction is as follows:

[0021]

[0022] Wherein, the acridin...

Embodiment 1

[0034] This embodiment provides a preparation method of florfenicol intermediate. The synthetic method of the florfenicol intermediate:

[0035] The compound A mentioned above is also D-(-)-threo-[p-(methylsulfonyl)phenyl]serine ethyl ester, the above-mentioned acridine salt visible light catalyst, diisopropylethyl The amine was added to anhydrous dichloroethane, and then the reaction environment was replaced with nitrogen three times, irradiated with a blue LED, and the reaction time was 20h. After the reaction, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a colorless white solid with a yield of 65%.

[0036] Wherein, the compound A, acridine salt, diisopropylethylamine and anhydrous dichloroethane are added in the following proportions: for every 2mL of anhydrous dichloroethane, add 0.2mmol, 1.0eq of the Compound A, 0.2mmol, 1.0eq of diisopropylethylamine, 0.02mmol, 0.1eq of acridine salt.

[0037] NMR and mass spectrometry o...

Embodiment 2

[0040] This embodiment provides a preparation method of florfenicol intermediate. The synthetic method of the florfenicol intermediate:

[0041] The compound A mentioned above is also D-(-)-threo-[p-(methylsulfonyl)phenyl]serine ethyl ester, the above-mentioned acridine salt visible light catalyst, diisopropylethyl The amine was added to anhydrous dichloroethane, and then the reaction environment was replaced with nitrogen three times, irradiated with a blue LED, and the reaction time was 20h. After the completion of the reaction, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a colorless white solid with a yield of 95%.

[0042] Wherein, the compound A, acridine salt, diisopropylethylamine and anhydrous dichloroethane are added in the following proportions: for every 2mL of anhydrous dichloroethane, add 0.2mmol, 1.0eq of the Compound A, 0.4mmol, 2.0eq of diisopropylethylamine, 0.02mmol, 0.1eq of acridine salt.

[0043] NMR and m...

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Abstract

The invention discloses a preparation method of a florfenicol intermediate. The preparation method includes subjecting D-(-)-threo-[para-(methyl sulfone)phenyl]serine ethyl esters to redox reaction ina solution containing acridine salt photocatalysts and reductants to generate the florfenicol intermediate. The preparation method of the florfenicol intermediate has the advantages that acridine salt serves as the photocatalysts, and carbonyl in the D-(-)-threo-[para-(methyl sulfone)phenyl]serine ethyl esters is reduced into hydroxyl with the presence of the reductants, so that side products arereduced effectively, yield of target products is increased, and synthesis cost is reduced.

Description

Technical field [0001] The invention belongs to the technical field of organic medicinal chemistry, and specifically relates to a preparation method of a florfenicol intermediate. Background technique [0002] Florfenicol is a broad-spectrum veterinary antibiotic that can be used to treat gram-positive, gram-negative and rickettsial infections in animals. [0003] Currently, some methods for preparing florfenicol are disclosed. For example, Nagabhushan uses the chloramphenicol intermediate D-(-)-threo-2-amino-1-[(p-nitro)phenyl]-1,3- Propylene glycol is used to prepare florfenicol; Tyson uses 9-step reaction to prepare florfenicol, but the total yield is low; Giordano et al. uses 4-step reaction to prepare florfenicol, the total yield is 50%, but it will still be resolved in the end. Synthesize florfenicol; then the Schering-Plough company in the United States uses the following chemical reaction formula as shown in the synthetic route to use the thiamphenicol intermediate D-(-)-t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/04
CPCC07B2200/07C07C315/04C07C317/32
Inventor 韩辉黄湧周海鹏张强韩珂珩丁小妹王雷锋余振辉弗朗西斯科·迪纳科·托斯特
Owner 深圳蓝新科技有限公司
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