138998-47-7

Basic information

• Product Name: ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate
• Synonyms: ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate
• CAS NO: 138998-47-7
• Molecular Weight: 319.256
• Mol File: 138998-47-7.mol

Chemical Properties

• Boiling Point: 381.5±42.0 °C(Predicted)
• Density: 1.324±0.06 g/cm3(Predicted)
• CAS DataBase Reference: ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate(138998-47-7)
• EPA Substance Registry System: ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate(138998-47-7)

Safety Data

• Hazardous Substances Data: 138998-47-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate is used as a key intermediate in the synthesis of the drug Levofloxacin (L360000). Levofloxacin is the S-(-) form of Ofloxacin (O245750), a potent antibiotic effective against gram-negative organisms. The compound plays a crucial role in the development of this antibiotic, contributing to its antimicrobial properties and therapeutic applications.
Used in the Synthesis of Levofloxacin:
In the pharmaceutical industry, ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate is used as a synthetic building block for the production of Levofloxacin. This antibiotic is known for its broad-spectrum activity against various gram-negative bacteria, making it a valuable asset in the treatment of bacterial infections. The compound's unique structure allows for the efficient synthesis of Levofloxacin, enhancing its production and availability for medical use.

Upstream product

• 94695-48-4 2,3,4,5-tetrafluorobenzoyl chloride 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 1117-37-9 ethyl (E)-3-(dimethylamino)acrylate 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 783365-87-7 ethyl 2-(2',3',4',5'-tetrafluorobenzoyl)-3-(N-aminobenzyldisulfide)-prop-2-enoate 
• 110943-79-8 Ethyl-3-(2-hydroxy-5-nitroanilino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylate 
• 216501-16-5 Ethyl 3-((3-Hydroxy(2-naphthyl))amino)-2-((2,3,4,5-tetrafluorophenyl)carbonyl)prop-2-enoate 
• 783366-13-2 5,6-Difluoro-3-oxo-10-phenyl-3H-pyrido[3,2,1-kl]phenoxazine-2-carboxylic acid 
• 783366-12-1 Ethyl 5,6-difluoro-3-oxo-10-phenyl-3H-pyrido[3,2,1-kl]phenoxazine-2-carboxylate 
• 783365-83-3 1,2-difluoro-4-oxo-4H-pyrido[3,2,1-kl]-8-phenyl-phenoxazine-5-carboxylic acid 
• 783365-82-2 ethyl 1,2-difluoro-4-oxo-4H-pyrido[3,2,1-kl]-8-phenyl-phenoxazine-5-carboxylate 
• 177472-30-9 C₂₀H₂₄FN₃O₄ 
• 112811-71-9 ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 106939-34-8 ethyl (S)-(-)-9,10-Difluoro-3-Methyl-7-Oxo-2,3-Dihydro-7H-Pyrido[1,2,3-de]-[1,4]Benzoxazine-6-Carboxylate 
• 100986-85-4 levofloxacin 
• 100986-89-8 levofloxacin Q-acid 
• 1263191-64-5 1-(1-carboxy-2-phenylethyl)-6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1263191-63-4 1-(carboxy(phenyl)methyl)-6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

Preparation method of levofloxacin and intermediates thereof

The invention relates to a preparation method of levofloxacin and intermediates thereof, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps of: carrying out amino substitution and ring closing reaction on an intermediate substrate to integrate a plurality of intermediates into a one-pot reaction, and hydrolyzing under an acidic condition to obtainlevofloxacin. According to the method provided by the invention, the intermediates do not need to be separated, the reaction operation is simplified, the production period is greatly shortened, multiple times of after-treatment are not needed, emission of three wastes is reduced, the method is more environmentally friendly, the reaction yield is increased compared with the prior art, and the method is suitable for industrial amplification.

Preparation method of levofloxacin and intermediates thereof

The invention relates to a preparation method of levofloxacin and intermediates thereof, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps of: carrying out amino substitution and ring closing reaction on a fluorine-substituted substrate to integrate a plurality of intermediates into a one-pot reaction, and hydrolyzing under acidic conditions to obtain levofloxacin. According to the method, the reaction operation is simplified, the production period is greatly shortened, multiple times of after-treatment are not needed, emission of three wastes is reduced, the method is more environmentally friendly, the reaction yield is increased by about 20% compared with the prior art, and the method is suitable for industrial amplification.

Improved method of preparation process of oxo-fluoro cyclization ester or levo-oxo-fluoro cyclization ester

The invention discloses an improved method of a preparation process of oxo-fluoro cyclization ester or levooxo-fluoro cyclization ester. Existing preparation methods of some levofloxacin intermediateshave many side reactions and are low in yield. According to the technical scheme in the invention, by means of 2,3,4,5-tetrafluorobenzoyl chloride, N,N-dimethylaminoethyl acrylate and (L-)aminopropanol as starting raw materials and toluene and N, N-dimethylformamide added with a water removal agent organic ester or anhydride as solvents, the oxygen-fluorine cyclization ester is prepared through aone-pot reaction. According to the method, organic ester or anhydride is added, so that the loss of raw materials and the generation of by-products are reduced, the reaction yield is increased, the product quality is ensured, and the yield of the (L-)oxo-fluoro cyclization ester can be increased from 75-80% to about 90%.

Environment-friendly method for preparing levofloxacin hydrochloride

The invention provides an environment-friendly method for preparing levofloxacin hydrochloride. The method comprises the following steps: preparing 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate, preparing levo-oxy main naphthenic acid, and preparing the levofloxacin hydrochloride. The method provided by the invention is concise, low in production cost, high in product yield, good in quality, economic and environment-friendly, fewer three wastes are discharged, and most byproducts are effectively separated and recycled, so that the method is convenient for industrial production and has great popularization significance.

Method for preparing high-quality levofloxacin hydrochloride

The invention provides a method for preparing high-quality levofloxacin hydrochloride. The method comprises the following steps: preparation of 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate, preparation of levo naphthenic acid and preparation of levofloxacin hydrochloride; the method is concise, the production cost is low, the product yield is high, quality is good, the method has the advantages of economic performance and environmental protection, three waste discharge capacity is little, effective separating and recycling on most by-product can be simultaneously realized, the method is convenient for industrial production, and has large popularization meaning.

Synthesis process of levofloxacin acid ester

The invention discloses a synthesis process of levofloxacin acid ester, comprising the following steps: (1) sequentially putting toluene, organic alkali and acyl chloride into an acylation reaction kettle, starting stirring, then adding N,N-dimethylaminoethyl acrylate into a dropping device, starting stirring and dropping, and then heating and stirring after dropping is completed; (2) after the completion of step (1), adding L-amino propanol, adding saturated salt water after the completion of reaction, adjusting the PH value through dropping, implementing static stratification after the PH value is stable, recovering toluene from a toluene layer in a decompression mode until no toluene solution exists in the reaction kettle, adding DMF, stirring and dissolving, and then transferring to a cyclization kettle head tank for later use; (3) adding DMF into a cyclization kettle, stirring, adding KF, heating to recover front cut fractions at atmospheric pressure, adding an amination reaction solution, and heating to maintain continuous refluxing; and (4) ending heat preservation, cooling, recovering DMF in a decompression mode, adding high-purity water after recovery, stirring, filtering, washing with the high-purity water, rinsing with methanol, and drying to obtain a product. The synthesis process disclosed by the invention adopts one-pot reaction, and is mild in reaction condition, simpler to operate and high in utilization rate of raw materials.

Method for preparing levofloxacin hydrochloride

The invention provides a method for preparing levofloxacin hydrochloride. The method comprises preparation of 3-(2-hydroxyl-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate, preparation of levo-oxygen main naphthenic acid, and preparation of the levofloxacin hydrochloride. The method is simple, low in production cost, high in product yield, good in product quality, economical, environmentally friendly, and low in three-waste emission load, and realizes effective separation and recycling of most byproducts, is convenient for industrial production and has great significance of promotion.

The simple synthesis and antimicrobial activity of novel fluoroquinolone derivatives from natural amino acid salts

A simple synthetic route was developed to prepare novel fluoroquinolone derivatives from amino acid salts. A facile route preparing the quinolone intermediates in one pot was explored which can facilitate the industrial operation. A series of new compounds were prepared conveniently and characterized by IR, 1H NMR, MS, and elemental analysis. The preliminary bioassays results revealed that they have certain antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, and Aspergillus fumigatus. Springer Science+Business Media, LLC 2010.

Quinolone dimers as potential antibacterial agents

A series of novel 6-fluoro1,4-dihydro-4-oxo-3-quinoline carboxylic acid dimers (34-37), were synthesized as potential antibacterial agents from commercially available fluoro benzoic acids.

HYDRAZIDE COMPOUNDS AND USES THEREOF

This application relates to certain novel polycyclic compounds that interact with quadruplex-forming regions of polynucleotides and thereby inhibit translation of genetic information into polypeptides. These compounds can thus provide anticancer and antibacterial and antiviral effects. The invention includes novel compounds and pharmaceutical compositions, and methods of using them to treat cancer and other conditions.