108656-33-3

Usage

Uses

Used in Veterinary Medicine:
Florfenicol Amine, Hydrochloride is used as an antibacterial agent for the treatment of bacterial infections in animals. It is particularly effective against a wide range of bacterial pathogens, making it a valuable tool in veterinary medicine.
Used in Florfenicol Production:
Florfenicol Amine, Hydrochloride serves as an intermediate in the production of Florfenicol (F405750), which is an important antibacterial agent used in the veterinary industry. Its role in the synthesis process highlights its significance in the development of effective treatments for bacterial infections in animals.
Used in Pharmacokinetic Studies:
Florfenicol Amine, Hydrochloride is utilized in the study of the pharmacokinetics of Florfenicol and its metabolites in edible tissues from domestic animals. This research is crucial for understanding the absorption, distribution, metabolism, and excretion of the antibiotic, ultimately contributing to the safe and effective use of Florfenicol in veterinary medicine.

InChI:InChI=1/C10H14FNO3S.ClH/c1-16(14,15)8-4-2-7(3-5-8)10(13)9(12)6-11;/h2-5,9-10,13H,6,12H2,1H3;1H/t9-,10-;/m1./s1

Upstream product

• 31925-26-5 threo-2-amino-3-hydroxy-3-(4-(methylsulfonyl)phenyl)propanoic acid 
• 40913-92-6 4-methylsulfonylbenzoyl chloride 

Relevant academic research and scientific papers

Florfenicol intermediate synthesis method

The invention belongs to the field of synthesis of pharmaceutical raw materials, and specifically discloses a florfenicol intermediate synthesis method, which comprises: (1) carrying out a reaction ona compound (II) and an acylating reagent in an organic solvent to form a compound (III); (2) carrying out a reaction on the compound (III) and an oxidizing agent in an organic solvent in the presenceof a catalyst to form a compound (IV); (3) carrying out a reaction on the compound (IV) and a fluorinating reagent in an organic solvent to form a compound (V); and (4) carrying out acidolysis on thecompound (V) in an organic solvent, and carrying out deprotection to obtain a compound (I), wherein various groups in the formulas are defined in the specification. According to the present invention, the florfenicol intermediate can be used for preparing florfenicol; and the method has characteristics of novel design, mild conditions and simple operation, and is suitable for industrial production.

Synthetic method of florfenicol intermediate

The invention relates to a synthetic method of a florfenicol intermediate. The synthetic method comprises following specific steps: compound II is dissolved in an organic solvent, under alkaline conditions, methyl sulfonyylation is carried out so as to obtain compound III; the compound III is subjected to ring closing reaction under alkaline conditions so as to obtain compound IV; and the compoundIV is subjected to fluorination ring opening reaction so as to obtain the florfenicol intermediate I. The synthetic method is novel in design, mild in conditions, and convenient in operation, and issuitable for industrialized production.

Asymmetric Synthesis of Florfenicol by Dynamic Reductive Kinetic Resolution with Ketoreductases

A chemoenzymatic synthesis of the veterinary antibiotic florfenicol is described. The key step involves the dynamic reductive kinetic resolution (DYRKR) of a keto ester by using a ketoreductase-02 (KRED-02) to afford the two contiguous stereocenters of the (2S,3R)-cis-1,2-amino alcohol intermediate in >99 % ee and a diastereomeric ratio (dr) of 99 %. This green biocatalysis is environmental friendly with high enantioselectivity and product yields. Two methods for the nucleophilic fluorination step involved the use of aziridines and cyclic sulfates to safely prepare fluoroamines with high regioselectivity. Additional studies have indicated that KRED-02 can also be used to afford chiral alcohol (S)-21 in good yields with high enantioselectivity. This study shows that the integration of biocatalysis into organic synthesis can be useful and provide industrial opportunities for applications of florfenicol.

Method for synthesis of florfenicol

The invention discloses a method for synthesis of florfenicol and belongs to the technical field of medicine synthesis. 1-R1-2-(R)-4- methylsulfino phenyl formyl aziridine is dissolved in solvent to react with sterically hindered reductant to form chiral alkamine compound 1 with a single configuration; compound 1 is heated and reacts with triethylamine hydrofluoride in the solvent to form (1R, 2S)-3-fluoride-1-4-(methylsulfino phenyl)-2-(R1-amido)-1-propyl alcohol; (1R, 2S)-3-fluoride-1-4-(methylsulfino phenyl)-2-(R1-amido)-1-propyl alcohol has the blocking group taken away in the solvent to form (1R 2S)-2-amido-3-fluoride-1-4-methylsulfino phenyl-1-propyl alcohol; florfenicol can then be obtained through dichloro-acetylation reaction of (1R, 2S)-2-amido-3-fluoride-1-4-methylsulfino phenyl-1-propyl alcohol.