(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

Name: (R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
Brand: ChemScene
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CAS No. 149524-42-5
Cat. No. CS-M1496
Purity≥98%
MDL No.MFCD08234640

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(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one|CS-M1496

Structure of 149524-42-5

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General Information

CAS No. 149524-42-5
Cat. No. CS-M1496
Purity ≥98%
MDL No. MFCD08234640
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₀FNO₃
Molecular Weight 211.19
Synonym(s) Tedizolid Impurity 33
SMILES FC1=CC=CC(N2C[C@@](CO)([H])OC2=O)=C1

Description

(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one features a chiral oxazolidinone core with a fluorinated phenyl group and a hydroxymethyl side chain, enabling selective integration into asymmetric synthesis. The pendant hydroxyl group supports derivatization while maintaining stability under standard bench conditions. This configuration enhances stereocontrol in catalytic transformations.

Application

(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one serves as a versatile chiral building block for medicinal chemistry, enabling efficient access to β-amino alcohol scaffolds via reductive cleavage or functionalization of the oxazolidinone ring. Its bench-stable nature and tolerance to common reaction conditions facilitate straightforward derivatization, while the hydroxymethyl group supports further transformations such as oxidation, protection, or coupling reactions in multi-step syntheses.

Synthesis

Route1
- 60456-26-0
- In-stock
  
  149524-47-0
- ~70%
- In-stock
  
  149524-42-5
References
- Im, Weon Bin; Choi, Sun Ho; Park, Ju-Young; Choi, Sung Hak; Finn, John; Yoon, Sung-Hwa European Journal of Medicinal Chemistry, 2011 , vol. 46, # 4 p. 1027 - 1039
Route2
- 60456-26-0
- ~72%
- In-stock
  
  149524-42-5
References
- DONG-A PHARM.CO.,LTD. Patent: WO2005/58886 A1, 2005 ; Location in patent: Page/Page column 24 ;
Route3
- 372-19-0
- ~%
- In-stock
  
  149524-42-5
References
- European Journal of Medicinal Chemistry, , vol. 46, # 4 p. 1027 - 1039

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 49.77
LogP 1.1432
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

CAS No. 149524-42-5

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