149524-42-5

Basic information

• Product Name: (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE
• Synonyms: (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE;(5R)-3-(3-Fluorophenyl)-5-hydroxymethyloxazolidin-2-one;(5R)-3-(3-fluorophenyl)-5-(hydroxyMethyl)-1,3-oxazolidin-2-one;2-Oxazolidinone, 3-(3-fluorophenyl)-5-(hydroxyMethyl)-, (5R)-
• CAS NO: 149524-42-5
• Molecular Formula: C₁₀H₁₀FNO₃
• Molecular Weight: 211.19
• Product Categories: pharmacetical
• Mol File: 149524-42-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 341.2 °C at 760 mmHg
• Flash Point: 160.1 °C
• Appearance: /
• Density: 1.368 g/cm³
• Vapor Pressure: 3.16E-05mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• PKA: 14.05±0.10(Predicted)
• CAS DataBase Reference: (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE(149524-42-5)
• EPA Substance Registry System: (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE(149524-42-5)

Safety Data

• Hazardous Substances Data: 149524-42-5(Hazardous Substances Data)

Usage

General Description

The chemical (R)-3-(3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one is a compound with a molecular formula of C10H11FO3N. It belongs to the class of oxazolidinones and is used as an intermediate in the synthesis of pharmaceuticals. (R)-3-(3-FLUOROPHENYL)-5-(HYDROXYMETHYL)OXAZOLIDIN-2-ONE has potential therapeutic applications in the treatment of bacterial infections due to its antibacterial properties. Additionally, it can be used in research and development for the synthesis of new drugs. As a chiral compound, it exists in two enantiomeric forms, with the (R)-enantiomer having specific stereochemical and biological properties. The chemical structure of (R)-3-(3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one makes it an important building block in the development of pharmaceuticals and other bioactive compounds.

InChI:InChI=1/C10H10FNO3/c11-7-2-1-3-8(4-7)12-5-9(6-13)15-10(12)14/h1-4,9,13H,5-6H2/t9-/m1/s1

Upstream product

• 60456-26-0 (R)-glycidyl butyrate 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 404-71-7 1-fluoro-3-isocyanatobenzene 
• 372-19-0 meta-fluoroaniline 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 121906-41-0 (S)-3-(Butoxy)-1,2-epoxypropane 
• 72755-13-6 (3-fluoro-phenyl)-carbamic acid methyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 139071-79-7 (S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 677727-18-3 C₃₁H₃₃FN₂O₅Si 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 380380-55-2 [(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate 
• 149524-44-7 (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide 
• 380380-56-3 (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one 
• 1333991-97-1 C₂₃H₁₈F₂N₆O₃ 
• 1333992-00-9 C₂₂H₁₈FN₇O₃ 
• 1333992-01-0 C₂₃H₁₉FN₆O₃ 
• 1333992-03-2 C₂₄H₂₁FN₆O₄ 
• 1333992-05-4 C₂₁H₁₇FN₆O₃S 
• 149524-45-8 (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide 
• 856866-72-3 (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one 

Relevant articles and documents

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.

A oxazolidinone compounds of preparation method (by machine translation)

The invention provides a oxazolidinone compounds of the preparation method. Specifically provides the type 1 compound preparation method. The formula 1 compound preparation method comprises, formula 2 N - methyl - D - grape amine compound in the presence of a catalytic reduction, direct formula 1 compound. The present invention provides a preparation has simplified the reaction step, shorten the reaction route, can make the final yield of the product is higher, and, better purity. (by machine translation)

Method for preparing tedizolid phosphate

The invention relates to the technical field of preparation of tedizolid phosphate, and especially relates to a preparation method of tedizolid phosphate. According to the invention, 3-fluoroaniline is taken as a raw material, and is subjected to a nucleophilic substitution reaction with (R)-(-)-glycidyl butyrate, then a cyclization reaction and hydrolysis are carried out, protective group is removed to obtain a compound (VI); the compound (VI) is subjected to an iodination reaction and the nucleophilic substitution reaction to obtain a compound (VIII); the compound (VIII) and 2-(1-methyl-tetrazolium-5-group)-5-bromopyridine (IX) are reacted, and then a target product (I) is obtained with phosphoric acid. The method has the advantages of short route, mild reaction condition, and easy post-treatment, and is more suitable for industrial production requirement.