174649-09-3

Basic information

• Product Name: (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate
• Synonyms: (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate;(R)-[3-(3-Fluoro-4-Morpholinophenyl)-2-oxo-5-oxazolidinyl]Methyl Methanesulfonat;(R)-(3-(3-flouro-4-Morpholinophenyl)-2-oxo-5-oxazolidinyl)Methyl Methanesulfonate;(R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate;(5R)-3-[3-Fluoro-4-(4-Morpholinyl)phenyl]-5-[[(Methylsulfonyl)oxy]Methyl]-2-oxazolidinone;2-Oxazolidinone, 3-[3-fluoro-4-(4-Morpholinyl)phenyl]-5-[[(Methylsulfonyl)oxy]Methyl]-, (5R)-;Linezolid related Compound;Linezolid USP RC D
• CAS NO: 174649-09-3
• Molecular Formula: C₁₅H₁₉FN₂O₆S
• Molecular Weight: 374.3845632
• EINECS: 1592732-453-0
• Mol File: 174649-09-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 183-185℃
• Boiling Point: 592.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.418
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 5.71±0.40(Predicted)
• CAS DataBase Reference: (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate(174649-09-3)
• EPA Substance Registry System: (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate(174649-09-3)

Safety Data

• Hazardous Substances Data: 174649-09-3(Hazardous Substances Data)

Usage

Uses

(5R)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone (Linezolid USP Related Compound D) is an intermediate in the synthesis of Linezolid Dimer (L466520), an impurity of the antibacterial agent Linezolid (L466500).

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 168828-82-8 (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol 
• 912552-54-6 (3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester 
• 912552-56-8 ((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester 
• 496031-56-2 (R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate 
• 868405-66-7 N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline 
• 565176-83-2 N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline 
• 168828-81-7 benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate 
• 239438-39-2 C₃₁H₃₆F₂N₄O₈ 
• 239438-43-8 C₂₈H₃₂F₂N₄O₈ 
• 905945-96-2 (R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol 
• 2689-39-6 3-fluoro-4-(4-morpholinyl)nitrobenzene 
• 369-34-6 3,4-difluoronitrobenzene 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 

Downstream Products

• 168828-84-0 (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one 
• 503026-31-1 (R)-[N-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl N,O-bis(tert-butoxycarbonyl)hydroxylamine 
• 1215006-09-9 (S)-5-((tert-octylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 1215006-08-8 (S)-5-((tert-butylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 1215006-07-7 (S)-5-((allylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 1236077-59-0 (5S)-(N)-[[(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl]methyl]bromide 
• 168828-89-5 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione 
• 165800-03-3 linezolid 

Relevant articles and documents

Synthesis of covalent bonding MWCNT-oligoethylene linezolid conjugates and their antibacterial activity against bacterial strains

Nowadays, infectious diseases caused by drug-resistant bacteria have become especially important. Linezolid is an antibacterial drug active against clinically important Gram positive strains; however, resistance showed by these bacteria has been reported. Nanotechnology has improved a broad area of science, such as medicine, developing new drug delivery and transport systems. In this work, several covalently bounded conjugated nanomaterials were synthesized from multiwalled carbon nanotubes (MWCNTs), a different length oligoethylene chain (Sn), and two linezolid precursors (4and7), and they were evaluated in antibacterial assays. Interestingly, due to the intrinsic antibacterial activity of the amino-oligoethylene linezolid analogues, these conjugated nanomaterials showed significant antibacterial activity against various tested bacterial strains in a radial diffusion assay and microdilution method, including Gram negative strains asEscherichia coli(11 mm, 6.25 μg mL?1) andSalmonella typhi(14 mm, ≤0.78 μg mL?1), which are not inhibited by linezolid. The results show a significant effect of the oligoethylene chain length over the antibacterial activity. Molecular docking of amino-oligoethylene linezolid analogs shows a more favorable interaction of theS2-7analog in the PTC ofE. coli.

Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives

Research activities on the oxazolidinone antibacterial class of compounds continue to focus on developing newer derivatives with improved potency, broad-spectrum activity and safety profiles superior to linezolid. Among the safety concerns with the oxazolidinone antibacterial agents is inhibition of monoamine oxidases (MAO) resulting from their structural similarity with toloxatone, a known MAO inhibitor. Diverse substitution patterns at the C-5 position of the oxazolidinone ring have been shown to significantly affect both antibacterial activity and MAO inhibition to varying degrees. Also, the antibacterial activity of compounds containing iron-chelating functionalities, such as the hydroxamic acids, 8-hydroxyquinolines and catechols have been correlated to their ability to alter iron intake and/or metabolism. Hence a series of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives were synthesized and evaluated for their antibacterial and MAO-A and -B inhibitory activities. The compounds were devoid of significant antibacterial activity but most demonstrated moderate MAO-A and -B inhibitory activities. Computer modeling studies revealed that the lack of potent antibacterial activity was due to significant steric interaction between the hydroxamic acid N-OH oxygen atom and one of the G2540 5′-phosphate oxygen atoms at the bacterial ribosomal binding site. Therefore, the replacement of the 5-acetamidomethyl group of linezolid with the 5-(N-hydroxyacetamido)methyl group present in the hydroxamic acid oxazolidinone derivatives was concluded to be detrimental to antibacterial activity. Furthermore, the 5-(hydroxamic acid)methyl oxazolidinone derivatives were also less active as MAO-A and -B inhibitors compared with linezolid and the selective inhibitors clorgyline and pargyline. In general, the 5-(hydroxamic acid)methyl oxazolidinone derivatives demonstrated moderate but selective MAO-B inhibitory activity.

PROCESS FOR THE PREPARATION OF CRYSTALLINE LINEZOLID

The present invention discloses a stable crystalline Form-I of linesolid process for preparation thereof.