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CS-W001157 4
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(S)-1-Cbz-pyrrolidine-3-carboxylic acid

  • CAS No. 192214-00-9

  • Cat. No. CS-W008576
  • Purity≥98%
  • MDL No.MFCD09608053

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

(S)-1-Cbz-pyrrolidine-3-carboxylic acid|CS-W008576

Structure of 192214-00-9

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General Information

  • CAS No. 192214-00-9
  • Cat. No. CS-W008576
  • Purity ≥98%
  • MDL No. MFCD09608053
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅NO₄
  • Molecular Weight 249.26
  • Synonym(s) (S)-1-((Benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid
  • SMILES O=C(OCC1=CC=CC=C1)N(CC2)C[C@H]2C(O)=O

Description

(S)-1-Cbz-pyrrolidine-3-carboxylic acid is a chiral building block featuring a pyrrolidine core with a Cbz-protected amine and a carboxylic acid at the 3-position. This configuration enables direct incorporation into peptide synthesis and medicinal chemistry campaigns, where stereochemical control is critical. The Cbz group provides stable protection under standard coupling conditions, facilitating selective functionalization and downstream deprotection without racemization.

Application

(S)-1-Cbz-pyrrolidine-3-carboxylic acid serves as a versatile chiral building block in medicinal chemistry, enabling efficient access to pyrrolidine-containing scaffolds prevalent in bioactive molecules. The Cbz group provides excellent stability and orthogonal deprotection compatibility, while the carboxylic acid facilitates coupling reactions. Its defined stereochemistry ensures high fidelity in asymmetric synthesis, making it ideal for peptide-like motifs and heterocyclic core construction.

Synthesis

  • Route1
    • null|null
      501-53-1
    • Benzyl (3S)-3-cyano-1-pyrrolidinecarboxylate|CS-0028278
      193693-69-5
    • ~66%
    • In-stock
      (S)-1-Cbz-pyrrolidine-3-carboxylic acid|CS-W008576
      192214-00-9

    References

    • FOB SYNTHESIS; CHOI, Woo-Baeg; KIM, Deog-Il; GRUSZECKA-KOWALIK, Ewa; JOO, Hyung-Yeul; LIU, Shuangpei; MAO, Shuli; LI, Yongfeng Patent: WO2011/160020 A2, 2011 ; Location in patent: Page/Page column 62 ;
  • Route2

    References

    • Mazzini; Lebreton; Alphand; Furstoss Journal of Organic Chemistry, 1997 , vol. 62, # 15 p. 5215 - 5218
  • Route3
    • null|null
      865704-61-6
    • ~79%
    • In-stock
      (S)-1-Cbz-pyrrolidine-3-carboxylic acid|CS-W008576
      192214-00-9

    References

    • Stoncius, Arvydas; Nahrwold, Markus; Sewald, Norbert Synthesis, 2005 , # 11 art. no. T12704SS, p. 1829 - 1837

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   66.84
  • LogP   1.7297
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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