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CS-W001157 4
Total: USD 88.00

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide

  • CAS No. 42267-27-6

  • Cat. No. CS-W006533
  • Purity≥95%
  • MDL No.MFCD11046652

*For research and further manufacturing use only, not for direct human use.

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide|CS-W006533

Structure of 42267-27-6

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General Information

  • CAS No. 42267-27-6
  • Cat. No. CS-W006533
  • Purity ≥95%
  • MDL No. MFCD11046652
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁F₃N₂O₄
  • Molecular Weight 268.19
  • Synonym(s) Nε-Trifluoroacetyl-Nα-carboxy-L-lysine Anhydride
  • SMILES O=C(NCCCC[C@@H]1NC(OC1=O)=O)C(F)(F)F

Description

This chiral amide features a trifluoromethyl group and a reactive oxazolidinone ring, enabling selective conjugation in synthetic workflows. The (S)-configured scaffold supports stereocontrolled transformations, while the bench-stable, moisture-tolerant structure simplifies handling in complex synthesis.

Application

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide serves as a versatile chiral building block for the synthesis of bioactive molecules, leveraging the oxazolidinone ring’s established role in asymmetric synthesis. Its trifluoroacetyl group enhances electrophilicity and provides a robust handle for selective transformations. The molecule exhibits excellent bench stability and facilitates efficient purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      112139-31-8
    • ~87%
    • In-stock
      (S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide|CS-W006533
      42267-27-6

    References

    • Blacklock; Shuman; Butcher; Shearin Jr.; Budavari; Grenda Journal of Organic Chemistry, 1988 , vol. 53, # 4 p. 836 - 844
  • Route2
    • null|null
      75-44-5
    • In-stock
      H-Lys(Tfa)-OH|CS-W012780
      10009-20-8
    • ~68%
    • In-stock
      (S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide|CS-W006533
      42267-27-6

    References

    • Cherevin; Gulevich; Popova; Zubreichuk; Knizhnikov Russian Journal of Organic Chemistry, 2007 , vol. 43, # 10 p. 1427 - 1431
  • Route3
    • In-stock
      H-Lys(Tfa)-OH|CS-W012780
      10009-20-8
    • null|null
      503-38-8
    • ~61%
    • In-stock
      (S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide|CS-W006533
      42267-27-6

    References

    • Huesmann, David; Birke, Alexander; Klinker, Kristina; Tuerk, Stephan; Raeder, Hans Joachim; Barz, Matthias Macromolecules, 2014 , vol. 47, # 3 p. 928 - 936

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   84.5
  • LogP   0.4702
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   5

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