Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
【 Providing a complete set of intermediates and impurities for Tedizolid 】
【 Providing a complete set of intermediates and impurities for Tedizolid 】
【 Providing a complete set of intermediates and impurities for Tedizolid 】
Product Specification: (5S)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
Chemical Identification
Chemical Name: (5S)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
Synonyms:
(S)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
(5S)-3-(4-Bromo-3-fluoro-phenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one
Oxazolidin-2-one, 3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-, (5S)-
CAS Registry Number: 1369530-77-7
Molecular Formula: C₁₀H₉BrFNO₃
Molecular Weight: 290.09 g/mol
Structural Characteristics
Core Structure: Oxazolidin-2-one ring.
Substituents:
At position 3: 4-Bromo-3-fluorophenyl ring (provides halogenated aromatic moiety).
At position 5: Hydroxymethyl group (-CH₂OH, a primary alcohol).
Stereochemistry: Chiral center at position 5 (carbon bearing the hydroxymethyl group) with defined S-configuration .
Physical Description
Appearance: Typically supplied as a white to off-white powder or crystalline solid.
Solubility: Soluble in common organic solvents (e.g., Dichloromethane (DCM), Chloroform (CHCl₃), Dimethylformamide (DMF), Dimethyl Sulfoxide (DMSO)). Moderately soluble or sparingly soluble in alcohols (Methanol, Ethanol). Generally insoluble in water.
Melting Point: Specific melting point data may vary between batches/suppliers. Typically reported in the range of ~110-130°C (uncertain, requires supplier specification).
Optical Rotation: Characteristic negative optical rotation is expected for the (5S)-enantiomer (e.g., [α]D²⁵ ~ -XX to -XX °, c=1 in solvent). [Exact value depends on purity and solvent; refer to CoA].
Storage: Store in a cool, dry place (typically 2-8°C or -20°C for long-term). Protect from light and moisture. Keep under inert atmosphere (e.g., N₂ or Ar) where possible to enhance stability.
Key Functional Groups & Reactivity
Oxazolidinone Ring: Relatively stable amide-like structure, but can be hydrolyzed under strongly acidic or basic conditions. Can act as a chiral auxiliary.
Hydroxymethyl Group (-CH₂OH): Primary alcohol functionality. Highly versatile for further chemical transformations:
Oxidation to aldehyde (-CHO) or carboxylic acid (-COOH).
Esterification or etherification.
Halogenation (e.g., to -CH₂Cl).
Protection (e.g., as silyl ether or acetate).
Aryl Bromide (C-Br): Enables palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Stille, Sonogashira, Buchwald-Hartwig amination) for introducing diverse substituents at the aromatic ring.
Aryl Fluoride (C-F): Relatively unreactive under many conditions but can participate in specific transformations (e.g., SNAr with strong nucleophiles) or influence electronic properties and binding.
Primary Applications
Pharmaceutical Intermediate: A key chiral building block in the synthesis of biologically active molecules, particularly antibiotics targeting resistant bacteria. It is a crucial intermediate in the synthesis of novel oxazolidinone-class antibiotics , such as specific analogs or development candidates related to Linezolid or Tedizolid , where modifications at the aryl ring (bromo/fluoro) and the C5 side chain are explored for improved potency, spectrum, or pharmacokinetics.
Medicinal Chemistry Research: Used in structure-activity relationship (SAR) studies exploring the oxazolidinone pharmacophore.
Organic Synthesis: Serves as a versatile chiral synthon due to its defined stereochemistry and multiple reactive handles (-CH₂OH, -Br).
Handling & Safety (General - ALWAYS consult SDS)
Hazard Statements (H-Codes): Typical anticipated hazards include:
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
H302: Harmful if swallowed.
Precautionary Statements (P-Codes): P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501.
Personal Protective Equipment (PPE): Safety glasses, chemical-resistant gloves (e.g., nitrile), lab coat. Use fume hood or adequate ventilation, especially when handling powders. Consider respiratory protection if dust generation is significant.
First Aid: Refer to specific SDS. Generally: Eyes - Flush with water. Skin - Wash with soap and water. Inhalation - Move to fresh air. Ingestion - Rinse mouth, seek medical attention.
