(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

Name: (S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 149524-45-8
Cat. No. CS-M1500
Purity≥98%
MDL No.MFCD09608095

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Type	HazMat Fee
Excepted Quantity	$0.00
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(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide|CS-M1500

Structure of 149524-45-8

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General Information

CAS No. 149524-45-8
Cat. No. CS-M1500
Purity ≥98%
MDL No. MFCD09608095
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₂FIN₂O₃
Molecular Weight 378.14
Synonym(s) None
SMILES FC1=C(I)C=CC(N2C[C@@](CNC(C)=O)([H])OC2=O)=C1

Description

This chiral oxazolidinone derivative features a sterically defined (S)-configured scaffold bearing a 3-fluoro-4-iodophenyl moiety and a pendant acetyl group. The iodine atom enables facile downstream coupling via cross-coupling chemistry, while the oxazolidinone ring provides conformational rigidity and enhanced stability under standard handling conditions. This structure serves as a key intermediate in the synthesis of bioactive molecules requiring precise stereochemical control.

Application

(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide serves as a versatile chiral building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. The oxazolidinone core enables stereoselective transformations, while the 3-fluoro-4-iodo-phenyl group supports palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with diverse functional groups facilitate efficient downstream derivatization in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  627543-03-7
- 108-24-7
- ~%
- In-stock
  
  149524-45-8
References
- Chen, Shili; Lou, Rongliang; Wu, Yusheng; Zhou, Jiacheng; Hanselmann, Roger Patent: US2010/234615 A1, 2010 ; Location in patent: Page/Page column 37-38 ;
Route2
- 519003-01-1
- 507-09-5
- ~%
- In-stock
  
  149524-45-8
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2004/56817 A1, 2004 ; Location in patent: Page 89 ; WO 2004/056817 A1
Route3
- 380380-55-2
- ~%
- In-stock
  
  149524-45-8
References
- Khera, Manoj Kumar; Cliffe, Ian A.; Prakash, Om Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 18 p. 5266 - 5269

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-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 58.64
LogP 1.8916
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Amide

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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(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

CAS No. 149524-45-8

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