- Synthesis method of florfenicol
-
The invention discloses a synthesis method of florfenicol, which comprises the following steps: by using (4R,5R)-2-dichloromethyl-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-4-oxazolemethanol (compound Ifor short) as a reaction raw material, carrying out chlorination, fluorination and hydrolysis to obtain florfenicol. The method has the advantages of cheap and easily available raw materials, simpleprocess operation, environmental protection and no pollution, accords with the industrialization concept of green production, and has extremely high industrialization value.
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Paragraph 0063-0065
(2021/03/24)
-
- METHODS FOR PREPARING FLORFENIOL AND INTERMEDIATE THEREOF
-
The present invention discloses a method for preparing florfenicol and its intermediate (V), comprising an addition reaction, a ring closure reaction, a hydrolysis reaction, a ring opening reaction, a reduction reaction, a ring reaction, a fluorination reaction and a ring opening reaction. In the present method for preparing florfenicol, respective reaction steps can be continuously operated, therefore the methods of the present invention features simplified process and shorter synthetic route, and obtained florfenicol has high chiral purity and is of high yield. The method of the present invention for preparing florfenicol (TM) using the intermediate (V) avoids waste water pollution and reduces the cost for treating wastewater and alleviates environmental pollution. At the same time, the methods of the present invention eliminates a chiral resolution procedure, thus increasing the utilization rate of atoms in the reaction. As a result, cost is reduced and process is simplified.
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Paragraph 0130; 0131
(2021/07/02)
-
- Method for continuously preparing florfenicol based on micro-reaction system
-
The invention provides a method for continuously preparing florfenicol based on a micro-reaction system. The preparation method comprises the following steps: respectively pumping an organic solution of a raw material {(4R, 5R)-2-(dichloromethyl)-5-[4-(methylsulfonyl) phenyl]-4, 5-dihydrooxazole-4-yl} methanol and an organic solution of a fluorinating reagent into a micro-mixer for mixing; introducing into a first micro-channel reactor for continuous fluorination reaction, and concentrating; obtaining a crude product; dissolving the crude product in alcohol and water, pumping into a second microchannel reactor, carrying out continuous hydrolysis ring-opening reaction, and separating and purifying a reaction product to obtain a florfenicol product. According to the method provided by the invention, the reaction time is only several minutes, the yield of the product florfenicol is greater than 95%, the operation is convenient, continuous and controllable, the amplification effect is avoided, the efficiency of the technological process is high, and the method has a very good industrial application prospect.
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-
Paragraph 0053-0054; 0057-0061; 0065-0068; 0072-0075; ...
(2021/07/24)
-
- Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol
-
A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.
- Chen, Fener,Cheng, Dang,Huang, Huashan,Jiang, Meifen,Liu, Minjie,Qu, Hongmin,Xia, Yingqi,Xiong, Tong,Zhang, Yan
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p. 11557 - 11570
(2021/09/02)
-
- Florfenicol synthesis method
-
The invention relates to a florfenicol synthesis method. The method comprises the step of carrying out a ring opening reaction on a product obtained by fluorinating a compound I by using sulfuryl fluoride as a fluorination reagent in a water-containing system to easily prepare florfenicol. The method has the advantages of simple operation, few by-products, safety, environmental protection, low production cost and the like, and is very suitable for industrial use.
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-
Paragraph 0106-0109; 0110-0112; 0113-0116
(2020/12/08)
-
- Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride
-
The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.
- Liu, Jinxin,Li, Yaling,Ke, Miaolin,Liu, Minjie,Zhan, Pingping,Xiao, You-Cai,Chen, Fener
-
p. 15360 - 15367
(2020/11/30)
-
- Synthetic method of florfenicol intermediate
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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.
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-
Paragraph 0139-0144
(2019/07/04)
-
- Florfenicol intermediate synthesis method
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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.
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-
-
- Method for preparing fluorinating reagent and fluoride continuously by microchannel reactor
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The invention discloses a method for preparing a fluorinating reagent and fluoride continuously by a microchannel reactor. The method comprises the following steps: introducing a mixed solution of amine and a solvent as well as fluorine-containing olefin into the microchannel reactor separately, performing reaction at the reaction temperature of subzero 20 to 30 DEG C for 30 to 180 seconds to prepare the fluorinating reagent, introducing the fluorinating reagent and a compound A into the microchannel reactor, performing mixing, heating and reaction to obtain a compound B, and performing hydrolysis reaction on the reaction liquid of the compound B to obtain a compound C. The method is simple to operate and safe to use, the use amount of the materials is greatly reduced, the process is environmentally-friendly and continuous, and the risk of high pressure and high temperature is avoided, so that high-yield continuous production of the fluorinating agent or fluoride is feasible. The comprehensive yield of the fluoride reaches 90 to 95 percent, basic quantitative reaction of the fluorinating reagent is realized and industrialized production is facilitated.
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-
Paragraph 0052; 0056; 0061; 0066; 0071; 0076; 0081; 0086
(2019/06/07)
-
- 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.
- Zou, Jie,Ni, Guowei,Tang, Jiawei,Yu, Jun,Jiang, Luobin,Ju, Dianwen,Zhang, Fuli,Chen, Shaoxin
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p. 5044 - 5053
(2018/10/05)
-
- Method for synthesis of florfenicol
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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.
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Paragraph 0056; 0063
(2017/08/27)
-
- Novel synthesis method of florfenicol
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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.
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-
Paragraph 0032; 0033
(2017/06/23)
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- FLORFENICOL SYNTHESIZING METHOD
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The present invention discloses a new florfenicol synthesizing method. The method synthesizes florfenicol products meeting requirements of the Drug Administration by a series of combinations of cyclization, selective reduction, fluorinated open ring, deprotection and acylation, hydroxyl sulfoacid esterified configuration converting reaction, hydrolysis reaction and the like. The synthesizing method of the present invention utilizing chiral amine closed-ring aziridine three-membered ring uses a physical separation method to repeatedly purify chiral aminoketone of high yield obtaining single R configuration, and uses selective reduction and converts the configuration to obtain florfenicol, greatly improving atom economy, while avoiding waste water pollution caused by the existing process, and greatly reducing costs for treating waste water and reducing pollution to the environment, thus lowering costs and simplifying the process. In addition, the present invention uses triethylamine hydrofluoride as a fluorinated open-ring reagent, to improve safety of a liquid reaction compared to a gas reaction and reduce corrosion of equipment, facilitating industrial production.
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-
Paragraph 0128; 0129
(2016/11/17)
-
- A substituted 1,2-aminoalcohols method for preparation of drug
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The invention discloses a preparation method of a substituted 1, 2-alkamine medicine. The preparation method comprises the following steps: dissolving a compound A into a solvent, then adding alkali, stirring, dripping a carbonylation agent, and after dripping, stirring, so as to obtain a compound B; dissolving the compound B into the solvent, adding a reducing agent, controlling the temperature of a reaction liquid to range from 10 DEG C below zero to 50 DEG C, and stirring, so as to obtain a compound C; adding the compound C into the solvent, using Ishikawa agent for fluoridation, after fluoridation, obtaining a compound D, removing the solvent, directly adding into acid for hydrolysis so as to obtain a compound E; resolving the compound E, ester and alkali into the solvent for reaction for 2 to 24 hours under a temperature of 0 to 50 DEG C, so as to obtain a compound F; the process route has the characteristics of short production period, low cost and high yield, the operation is simple and convenient, the product yield is increased while unit operation is shortened, and the preparation method is suitable for industrial production.
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Paragraph 0096; 0097
(2016/10/07)
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- Catalytic asymmetric transfer hydrogenation/dynamic kinetic resolution: an efficient synthesis of florfenicol
-
A robust and practical method has been developed for the synthesis of florfenicol (1) starting from commercial available 4-(methylsulfonyl) benzoic acid. The key step in this synthesis was the Ru-chloramphenicol base catalyzed asymmetric transfer hydrogenation of N-Boc α-amino-β-ketoester 5 through a dynamic kinetic resolution, which afforded the key chiral building block, anti-(2S,3S)-α-Boc-amino-β-hydroxyl ester 4, with high diastereoselectivity (92% de) and enantioselectivity (78% ee). The synthesis of a series of novel chloramphenicol base ligands L1–L10 is also included. This protocol could also be used for the asymmetric synthesis of fully synthetic analogs of florfenicol.
- Wang, Xinlong,Xu, Lingjun,Yan, Lingjie,Wang, Haifeng,Han, Sheng,Wu, Yan,Chen, Fener
-
p. 1787 - 1793
(2018/03/29)
-
- A novel no-carrier-added submicromolar scale radiosynthesis of [S-methyl-14C]-florfenicol
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In this paper is reported a novel reaction scheme for the no-carrier-added submicromolar scale radiosynthesis of [S-methyl-14C]-florfenicol that has been newly designed, developed and employed by us successfully. The [ 14C]-product was obtained in an overall radiochemical yield of 30% based on [14C]-methyl iodide taken for the reaction with a radiochemical purity of more than 96%. The specific activity of the product was ~50 mCi (1.85 GBq)/mmol. Chlorosulfonation of compound I was followed by sodium salt formation in situ and it was succeeded by the introduction of [ 14C]-methyl group by coupling with [14C]-CH3I. Subsequently, the oxazolidin-2-one protecting group was opened up by a reaction with sulfuric acid in dioxane and later, the amino group was dichloroacetylated with methyl-2,2-dichloroacetate in triethylamine to obtain [S-methyl- 14C]-florfenicol. A novel method employing a newly designed reaction scheme for the no-carrier-added submicromolar scale radiosynthesis of [S-methyl-14C]-florfenicol has been developed and reported in this paper. An overall radiochemical yield of 30% based on [14C]-methyl iodide was obtained. The radiochemical purity of the final product obtained was more than 96% and specific activity was ~50 mCi (1.85 GBq)/mmol. Copyright
- Srinivas,Prabhakar,Unny,Sudhakar,Mukkanti,Choudary
-
p. 382 - 384
(2013/08/23)
-
- An efficient enantioselective synthesis of florfenicol based on sharpless asymmetric dihydroxylation
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An efficient and highly enantioselective synthesis of florfenicol- via a new intermediate threo-dihydroxy ester, with a Sharpless asymmetric dihydroxylation as the key step, is reported. A ring-opening/reduction strategy avoids the formation of a chlorinated byproduct that occurs in Schumachers phenyloxazoline procedure. The overall yield of florfenicol by this new process is 23% based on 4-(methylsulfonyl)benzaldehyde. Georg Thieme Verlag Stuttgart · New York.
- Wang, Zhong-Hua,Zheng, Chen,Li, Feng,Zhao, Lei,Chen, Fen-Er,He, Qiu-Qin
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p. 699 - 704
(2012/04/04)
-
- An efficient enantioselective synthesis of florfenicol via a vanadium-catalyzed asymmetric epoxidation
-
An efficient and highly enantioselective synthesis of florfenicol 1 was achieved with 37% overall yield starting from commercially available 4-methylthiobenzaldehyde. A key feature of the synthesis is the vanadium-catalyzed asymmetric epoxidation of allylic alcohol 5 with aq tert-butyl hydroperoxide to form (2S,3S)-epoxide 6.
- Li, Feng,Wang, Zhong-Hua,Zhao, Lei,Xiong, Fang-Jun,He, Qiu-Qin,Chen, Fen-Er
-
experimental part
p. 1337 - 1341
(2011/11/29)
-
- An efficient enantioselective synthesis of florfenicol via asymmetric aziridination
-
An efficient enantioselective synthesis of florfenicol is accomplished in 44.7% overall yield from commercially available p-(methylsulfonyl)benzaldehyde. Key features of this synthesis are the asymmetric aziridination reaction mediated by the Wulff's catalyst in situ derived from (R)-VANOL and diastereoselectively ring-opening of (2S,3S)-fluoroaziridine 13.
- Wang, Zhonghua,Li, Feng,Zhao, Lei,He, Qiuqin,Chen, Fener,Zheng, Chen
-
experimental part
p. 9199 - 9203
(2011/12/01)
-
- A facile and efficient asymmetric synthesis of florfenicol
-
A facile and efficient enantioselective synthesis of flor-fenicol starting from commercially available 4-methylthiobenzaldehyde is described. Key features of the synthesis include a one-step oxidation of allyl and thioether groups in allylic alcohol to form (2S,3S)-epoxide under Sharpless epoxidation conditions and a highly efficient conversion of (1R,2R)-azide into amino alcohol via debenzylation and reduction of an azido moiety in one-pot operation. Georg Thieme Verlag Stuttgart. New York.
- Li, Feng,Wang, Zhong-Hua,Zhao, Lei,Chen, Fen-Er
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p. 2883 - 2885
(2012/01/11)
-
- PROCESS FOR PREPARING OXAZOLINE-PROTECTED AMINODIOL COMPOUNDS USEFUL AS INTERMEDIATES TO FLORFENICOL
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Processes for preparing oxazoline compounds are disclosed. These oxazoline compounds are useful intermediates in the preparation of Florfenicol and related compounds.
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-
Page/Page column 48-49
(2010/04/03)
-
- PROCESS FOR PREPARING OXAZOLIDINE- AND OXAZOLIDINONE-AMINODIOLS
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A method of preparing oxazolidine-protected and oxazolidinone-protected aminodiol compounds is disclosed. These compounds tend to be useful as intermediates in processes for making Florfenicol and related compounds.
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Page/Page column 31
(2009/03/07)
-
- Process for Recovering Florfenicol and Florfenicol Analogs
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This invention is generally directed to a method for recovering florfenicol and florfenicol analogs from pharmaceutical compositions. The recovered florfenicol and analogs can be, for example, reused to make new pharmaceutical compositions and thereby reduce the need and expense of manufacturing new florfenicol and florfenicol analogs.
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-
- New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: a chemo-enzymatic approach
-
Thiamphenicol and florfenicol have been synthesized stereoselectively from enantiomerically pure 4-methylsulfanyl-mandelonitrile, which was obtained by hydrocyanation reaction of 4-methylsulfanyl-benzaldehyde catalyzed by (R)-hydroxynitrile lyase of Badamu (Prunus communis L. var. dulcis Borkh, almond from Xinjiang, China). It was found to be a highly effective bio-catalyst for this reaction after an extensive screening.
- Lu, Wenya,Chen, Peiran,Lin, Guoqiang
-
p. 7822 - 7827
(2008/12/20)
-
- Process for preparing oxazolidine protected aminodiol compounds useful as intermediates to florfenicol
-
An improved method of preparing oxazolidine protected aminodiol compounds is disclosed. These compounds are useful intermediates in processes for making Florfenicol.
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Page/Page column 8-9
(2008/06/13)
-
- Process for the synthesis of intermediates of chloramphenicol or its analogues
-
The present invention relates to the synthesis of antibacterial compounds such as Chloramphenicol and its analogues Thiamphenicol and Florfenicol and particularly to a new reaction for the preparation of the intermediate compound aminodiolphenylsulfone. This reaction permits the introduction of modified residues to obtain modified antibiotics with an improved stability towards the action of bacterial resistant determinants. In addition, higher purities may be also obtained due to an improved procedure requiring fewer purification steps.
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Page/Page column 5
(2008/06/13)
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF FLORFENICOL
-
The present invention relates to a method for the preparation of Florfenicol from Fluoroamine compound, namely (1R,2S)-1-[4-(methylsulfonyl)phenyl]-2-amino-3-fluoro-1-propanol (II), by reaction with dihaloacetic acid ester in an organic solvent in presence of an inorganic base.
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Page/Page column 3-4
(2008/06/13)
-
- Process for preparing florfenicol
-
The present invention is directed to a new process of preparing highly pure Florfenicol. The invention is further directed to new oxazolidine derivatives useful in making Florfenicol and processes of making these derivatives. Examples of such intermediates include (4R,5R)-3-acetyl-2,2-dimethyl-4-hydroxymethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine; and (4S,5R)-3-acetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine.
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- FLORFENICOL PRODRUG HAVING IMPROVED WATER SOLUBILITY
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The present invention discloses phosphate esters of florfenicol (prodrugs) and florfenicol analogs having superior water solubility that are hydrolyzed to florfenicol or the respective florfenicol analog in vivo, upon administration to an animal.
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Page/Page column 20
(2008/06/13)
-
- Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-(p-toluenesulfinyl)aziridine 2-carboxylic acids
-
A concise, highly efficient asymmetric synthesis of aminopropanediol (1R,2R)-(-)-3, precursor to the broad spectrum antibiotics thiamphenicol/florfenicol 1/2, was prepared in two steps from cis-aziridine 2-carboxylic acid (2S,3S)-(-)-5.
- Davis, Franklin A.,Zhou, Ping
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p. 7525 - 7528
(2007/10/02)
-
- Process for the preparation of trans-(5R)-2,4,5-trisubstituted 2-oxazolines
-
A process for the preparation of 2,4,5-trisubstituted 2-oxazoline compounds having trans-(5R) configuration from precursors wherein the carbon atom that will be at position 5 in the oxazoline ring, has S configuration, is described.
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-
- 2-OXAZOLIDINONES AS REGIOSELECTIVE PROTECTION OF β-AMINO ALCOHOLS IN THE SYNTHESIS OF 2-AMINO-1-ARYL-3-FLUORO-1-PROPANOLS
-
The regioselective conversion of threo-2-ethoxycarbonylamino-1--1,3-propanediol, 4, into 4-hydroxymethyl-5--2-oxazolidinone, 8, is described as well as the use of this protection procedure in the synthesis of the fluoro analogue, 2, of thiamphenicol, 1.Methods of hydrolysis of the oxazolidinone ring are revisited for compound 11; new procedures via N-acylated intermediates have been investigated and their application is reported.
- Jommi, Giancarlo,Pagliarin, Roberto,Tavecchia, Paolo,Chiarino, Dario,Fantucci, Mario
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p. 485 - 490
(2007/10/02)
-
- PREPARATION OF 2--2,3-DIHYDROOXAZOLOISOINDOL-5(9bH)-ONE DERIVATIVES AND A NEW SYNTHESIS OF THIAMPHENICOL ANALOGUES
-
A new procedure of protection-deprotection of the amino group and, regioselectively, of the secondary hydroxyl in 2-amino-1--1,3-propanediol, 5, has been developed; this procedure facilitates the synthesis of thiamphenicol analogues with potential antibiotic activity.A new synthesis of the 3-fluoro analogue, 3, and the synthesis of intermediates potentially useful in the preparation of the 3-chloro, 3-bromo, 3-iodo, and 3-acetylthio analogues are described.
- Jommi, Giancarlo,Pagliarin, Roberto,Chiarino, Dario,Fantucci, Mario
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p. 653 - 658
(2007/10/02)
-
- 1-Aryl-2-acylamido-3-fluoro-1-propanol acylates, methods for their manufacture and intermediates useful therein, methods for their use as antibacterial agents and compositions useful therefor
-
Described are D-(threo)-1-aryl-2-acylamido-3-fluoro-1-propanol esters and salts thereof, methods for their preparation, and methods for their use as antibacterial agents.
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-
-
- 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor
-
Described are D-(threo)-1-aryl-2-acylamido-3-fluoro-1-propanols, methods for their preparation, and methods for their use as antibacterial agents. Of particular interest are D-(threo)-1-p-nitrophenyl-2-dichloroacetamido-3-fluoro-1-propanol and D-(threo)-1-p-methylsulfonylphenyl-2-dichloroacetamido-3-fluoro-1-propanol and the corresponding 2-difluoroacetamido compounds which are the 3-fluoro-3-deoxy analogs of chloramphenicol, thiamphenicol, difluoroacetyl analog of chloramphenicol, and of fluorthiamphenicol, respectively, and which are active both against organisms sensitive to and resistant to the parent amphenicol antibiotics. Other particularly valuable antibacterial agents include the corresponding 2-(chlorofluoroacetamido)-, 2-dichlorodeuterioacetamido, 2-difluorodeuterioacetamido-, and the 2-(chlorofluorodeuterioacetamido)- derivatives of the foregoing 3-fluoro-3-deoxy amphenicols.
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