947736-16-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[[(5R)-3-[3-Fluoro-4-(4-Morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]Methyl]-1H-isoindole-1,3(2H)-dione is used as a potential antimicrobial agent for the development of new drugs to combat resistant bacterial strains. Its unique structure and oxazolidinone class provide a foundation for further research into its efficacy against various pathogens.
Used in Chemical Research:
In the field of chemical research, 2-[[(5R)-3-[3-Fluoro-4-(4-Morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]Methyl]-1H-isoindole-1,3(2H)-dione serves as a subject for studying the synthesis and modification of complex organic molecules. Its properties and reactivity can be explored to understand the broader implications of its structure and to develop new synthetic pathways or applications in various chemical processes.

Upstream product

• 874340-08-6 N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1074-82-4 potassium phtalimide 
• 136918-14-4 phthalimide 
• 1373348-79-8 (S)-3-chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl chloroformate 
• 1373348-82-3 (S)-3-Chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl-3-fluoro-4-morpholinophenylcarbamate 
• 148857-42-5 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione 
• 868405-66-7 N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline 
• 168828-81-7 benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate 
• 224323-51-7 3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 68-12-2 N,N-dimethyl-formamide 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 

Relevant academic research and scientific papers

Linezolid preparation method

The invention relates to a linezolid preparation method. 3-fluoro-4-morpholinyl aniline is taken as a starting material and subjected to a reaction with (S)-(+)-N-(2,3-ethoxypropyl) phthalimide, an intermediate 1 is generated and subjected to a cyclization reaction with a carbonylation agent, an intermediate 2 is generated, an ammonolysis reaction and an acetylation reaction are performed, and a target compound is obtained. The problems of poor safety, strict conditions, many impurities and low yield, which are not suitable for industrial production, of a linezolid preparation method in the prior art are solved, the starting material of the route is cheap and available, the operation is simple, hazardous reagents are avoided, the solvent is easily recycled and reused, reaction yield is higher, purity of a final product is up to 99.9% or higher, and the linezolid preparation method is suitable for industrial production.

ONE POT SYNTHESIS FOR THE PREPARATION OF SUBSTITUTED PHTHALIMIDO OXAZOLIDINONE ANTIBACTERIALS AND OXAZOLIDINONE ANTIHAROMBOTICS COMPOUNDS BY USING RECYCLABLE HETEROGENEOUS CATALYST

A novel one pot and high yield process for the preparation of substituted phthalimidooxazolidinone compounds by using recyclable heterogeneous catalyst and preparation of oxazolidinoneantibacterials and oxazolidinoneantithrombotics thereof.

Process for the preparation of linezolid

The present invention relates to an improved process for the preparation of Linezolid. More specifically, the present invention relates to an improved process for preparing (S)—N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl] phthalimide and (S)-glycidyl phthalimide intermediates, which are used in the preparation of Linezolid.

AN IMPROVED PROCESS FOR THE PREPARATION OF LINEZOLID

The present invention relates to an improved process for the preparation of Linezolid. More specifically, the present invention relates to an improved process for preparing(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl] phthalimide and (S)-glycidyl phthalimide intermediates, which are used in the preparation of Linezolid.

A novel method for preparation of linezolid, (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl) methyl) acetamide

Background: Linezolid (I) [(S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl) methyl) acetamide] is a synthetic antibiotic used for the treatment of serious infections caused by grampositive bacteria that are resistant to other antibiotics. Linezolid empirical formula is C16H20FN3O4and its molecular weight is 337.35. It is active against most Gram-positive bacteria that cause disease, including streptococci, vancomycin-resistant enterococci (VRE), and methicillin-resistant Staphylococcus aureus (MRSA). The main uses are infections of the skin and pneumonia, although it may be used for a variety of other infections. Linezolid was discovered in the 1990s by a team at Pharmacia and Upjohn Company and first approved for use in 2000. Lohray et al., in 1999, have reported a synthetic method for Linezolid starting from D-mannitol, the chemical synthesis of Linezolid by alternate route has attracted several research groups in the past 15years. Methods: An improved and economically viable process is described to prepare Linezolid wherein methyl 3-fluoro-4-morphinolino phenyl carbamate (V) is reacted with R-epichlorohydrin in the presence of n-butyllithium in hexane to obtain (R)-5-(chloromethyl)-3-(3-fluoro-4-morpholinophenyl) oxazolidin-2-one (IV) which reacts with potassium phthalimide in presence of polar solvent to give (S)-2-[3-(3-3-fluoro-4-morpholin-4-yl-phenyl)-oxazolidine-5-yl methyl]-isoindole-1,3-dione (III), which is subsequently converted to Linezolid. Results: Linezolid was obtained via only four steps with yield 90% and high purity. This process avoids formation and use of sensitive intermediates. It is an improved process for the preparation of an intermediate (R)-5-(chloromethyl)-3-(3-fluoro-4-morpholinophenyl) oxazolidin-2-one (formula IV). Conclusion: Linezolid was successfully synthesized from (3-fluoro-4-morpholin-4-yl-phenyl)-carbamic ester via R-epichlorohydrin and potassium phthalimide and developed new intermediate (5R)-5-chloromethyl-3-(3-fluoro-4-morpholin-4-yl-phenyl) oxazolidin-2-one (IV). The present method relates to a novel, cost effective and industrially viable process. Thus, the process described is less cumbersome by way of reduced reaction stages, high purity and quantity of the yield. In comparison with previously reported synthetic strategies, this novel approach is believed to be the shortest and the most efficient synthetic route to date.

Preparation method of linezolid

The invention discloses a preparation method of linezolid. (S)-4-chloro-1,3-butanediol (compound 1) is taken as a raw material, and linezolid is obtained after potassium phthalimide substitution, Curtius rearrangement ring closure, Ullmann coupling, hydrazinolysis and amidation; a synthesis process causes small pollution and is easy to treat, the yield and purity in each step are high, and the method is environment-friendly, low in production cost and suitable for industrial production.

A process for the preparation of linezolid

The invention relates to a linezolid (1) preparation method. The method comprises the following steps: reacting a raw material 3,4-difluoronitrobenzene with morpholine, reducing, reacting with benzyl chloroformate to obtain N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline, carrying out a ring closure reaction of N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline and (S)-N-(2,3-epoxypropyl)phthalimide, ammonolyzing, and acetylating to obtain linezolid (1).

PROCESS FOR THE PREPARATION OF OXAZOLIDINONE DERIVATIVES

The present invention relates to an improved process for the preparation of Oxazolidinone derivatives. More specifically, the present invention relates to an improved process for preparing (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide, an intermediate used in the preparation of Oxazolidinone derivatives.

METHOD FOR PREPARING LINEZOLID INTERMEDIATE

Disclosed is a new method for preparing a methyl substitute of a linezolid intermediate, (S)-2-(3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazoline) (I), wherein the intermediate (I) is obtained by the cyclization of 3-fluoro-4-morpholinophenyl isocyanate (II) and epoxy compound (III). This process has a short process route, low cost, easy operation, and high yield, so is suitable for a large-scale industrial production.

PROCESS FOR PREPARATION OF LINEZOLID

The present invention discloses an in-situ process for preparation of Linezolid polymorphic Form II free of impurities.