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CS-W001157 4
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(S)-4,4-Difluoropyrrolidine-2-carboxylic acid

  • CAS No. 52683-81-5

  • Cat. No. CS-W021174
  • Purity≥95%
  • MDL No.MFCD10697866

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

(S)-4,4-Difluoropyrrolidine-2-carboxylic acid|CS-W021174

Structure of 52683-81-5

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General Information

  • CAS No. 52683-81-5
  • Cat. No. CS-W021174
  • Purity ≥95%
  • MDL No. MFCD10697866
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₇F₂NO₂
  • Molecular Weight 151.11
  • Synonym(s) proline, 4,4-difluoro-
  • SMILES O=C([C@H]1NCC(F)(F)C1)O

Description

(S)-4,4-Difluoropyrrolidine-2-carboxylic acid features a rigid pyrrolidine core with two fluorine atoms at the C4 position, conferring enhanced metabolic stability and altered electronic properties. This stereodefined building block integrates readily into peptidomimetics and bioactive compounds, offering improved membrane permeability and resistance to enzymatic degradation in medicinal chemistry applications.

Application

(S)-4,4-Difluoropyrrolidine-2-carboxylic acid serves as a conformationally constrained, bioisosteric surrogate for proline in peptide-based drug discovery. Its difluorinated pyrrolidine ring enhances metabolic stability and modulates backbone geometry, enabling improved target affinity and membrane permeability. The carboxylic acid functionality facilitates direct coupling in solid-phase synthesis, while the stereochemistry ensures predictable folding in cyclic peptides. This building block is bench-stable, readily purified by crystallization, and compatible with standard coupling protocols.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Company Patent: US2008/9497 A1, 2008 ; Location in patent: Page/Page column 109 ; US 20080009497 A1
  • Route2
    • null|null
      156046-01-4
    • ~44%
    • In-stock
      (S)-4,4-Difluoropyrrolidine-2-carboxylic acid|CS-W021174
      52683-81-5

    References

    • Burger, Klaus; Rudolph, Martin; Fehn, Susanna; Sewald, Norbert Journal of Fluorine Chemistry, 1994 , vol. 66, # 1 p. 87 - 90
  • Route3

    References

    • Demange, Luc; Menez, Andre; Dugave, Christophe Tetrahedron Letters, 1998 , vol. 39, # 10 p. 1169 - 1172

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

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Computational Chemistry Data

  • TPSA   49.33
  • LogP   0.0682
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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