444335-16-4

Basic information

• Product Name: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
• Synonyms: 2-Oxazolidinone,3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-, (5R)-;Torezolid Intermediate3;(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE;(5R)-3-(4-broMo-3-fluorophenyl)-5-(hydroxyMethyl)-1,3-oxazolidin-2-one;(R)-3-(4-BroMo-3-fluorophenyl)-5-(hydroxyMethyl)oxazolidin-2-one;(5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-onea
• CAS NO: 444335-16-4
• Molecular Formula: C₁₀H₉BrFNO₃
• Molecular Weight: 290.09
• EINECS: 1592732-453-0
• Product Categories: Tedizolid intermediates
• Mol File: 444335-16-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 401.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.701±0.06 g/cm3(Predicted)
• Refractive Index: 1.589
• Storage Temp.: 2-8°C
• PKA: 14.05±0.10(Predicted)
• CAS DataBase Reference: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(444335-16-4)
• EPA Substance Registry System: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(444335-16-4)

Safety Data

• Hazardous Substances Data: 444335-16-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one" is a derivative of oxazolidinone, a class of antibiotics commonly used to treat bacterial infections. This particular compound contains a hydroxymethyl group and a bromine-fluorine substituted phenyl ring. It has a specific stereochemistry, denoted by the (5R) configuration, which indicates the positioning of its substituents on the oxazolidinone ring. The presence of the bromo and fluoro groups suggests potential biological activity, and the hydroxymethyl group could also affect its reactivity and pharmacological properties. (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE may have potential applications in the development of new antibiotics or other pharmaceutical agents.

InChI:InChI=1/C10H9BrFNO3/c11-8-2-1-6(3-9(8)12)13-4-7(5-14)16-10(13)15/h1-3,7,14H,4-5H2/t7-/m1/s1

Upstream product

• 372-19-0 meta-fluoroaniline 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 
• 60456-26-0 (R)-glycidyl butyrate 
• 656-65-5 3-fluoro-4-bromophenylamine 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 288570-67-2 2-methylpropyl (4-bromo-3-fluorophenyl)carbamate 

Downstream Products

• 1188330-70-2 (R)-3-(4-bromo-3-fluoro-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-oxazolidin-2-one 
• 1401342-92-4 C₁₉H₂₂BFN₂O₆ 
• 504437-66-5 (S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide 
• 1401341-59-0 C₂₁H₂₁FN₆O₄ 
• 1401341-60-3 C₂₀H₂₁FN₆O₃*ClH 
• 1401341-61-4 C₂₁H₂₃FN₆O₃ 
• 1401341-63-6 C₂₄H₂₇FN₆O₅ 
• 1401341-64-7 C₂₂H₂₅FN₆O₄ 
• 1401341-65-8 C₂₃H₂₅FN₆O₃ 
• 1401341-66-9 C₂₃H₂₃FN₆O₃ 
• 1401341-67-0 C₂₆H₃₁FN₆O₅ 
• 1401341-69-2 C₂₂H₂₃FN₆O₅ 
• 1401341-70-5 C₂₄H₂₅FN₆O₆ 
• 1401341-71-6 C₂₆H₂₇FN₆O₈ 

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)

OXAZOLIDINONE HYDROXAMIC ACID COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

This invention pertains generally to treating bacterial infections using organic compounds of Formula I. In certain aspects, the invention pertains to treating infections caused by Gram-negative bacteria. (I) wherein X, Y, R1, R2, R3, R4 and R5 and defined herein.