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CS-W001157 4
Total: USD 88.00

Methyl 1-Cbz-azetidine-3-carboxylate

  • CAS No. 757239-60-4

  • Cat. No. CS-0028270
  • Purity≥95%
  • MDL No.MFCD11110708

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

Methyl 1-Cbz-azetidine-3-carboxylate|CS-0028270

Structure of 757239-60-4

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General Information

  • CAS No. 757239-60-4
  • Cat. No. CS-0028270
  • Purity ≥95%
  • MDL No. MFCD11110708
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅NO₄
  • Molecular Weight 249.26
  • Synonym(s) None
  • SMILES O=C(N1CC(C(OC)=O)C1)OCC2=CC=CC=C2

Description

Methyl 1-Cbz-azetidine-3-carboxylate features a conformationally constrained azetidine ring bearing a Cbz-protected amine and ester functionality, enabling direct incorporation into peptide backbones. The rigid scaffold imparts distinct stereochemical control in synthetic transformations, while the Cbz group ensures stable protection under standard conditions. This derivative streamlines access to bioactive heterocycles in medicinal chemistry campaigns.

Application

Methyl 1-Cbz-azetidine-3-carboxylate serves as a versatile chiral building block for synthesizing bioactive azetidine-containing compounds. The Cbz group provides stable protection of the nitrogen, enabling selective functionalization at the 3-position. It participates reliably in standard coupling reactions and facilitates efficient ring-opening or cyclization processes, making it well-suited for medicinal chemistry applications requiring precise stereocontrol and orthogonal reactivity.

Synthesis

  • Route1
    • null|null
      186581-53-3
    • In-stock
      1-Cbz-azetidine-3-carboxylic acid|CS-W004868
      97628-92-7
    • ~10%
    • In-stock
      Methyl 1-Cbz-azetidine-3-carboxylate|CS-0028270
      757239-60-4

    References

    • Zhu, Gui-Dong; Gong, Jianchun; Gandhi, Virajkumar B.; Penning, Thomas D.; Giranda, Vincent L. Patent: US2006/229289 A1, 2006 ; Location in patent: Page/Page column 19 ;
  • Route2
    • In-stock
      Methyl azetidine-3-carboxylate hydrochloride|CS-D1541
      100202-39-9
    • null|null
      501-53-1
    • ~%
    • In-stock
      Methyl 1-Cbz-azetidine-3-carboxylate|CS-0028270
      757239-60-4

    References

    • US2011/183960 A1, ; Page/Page column 27 ;
  • Route3
    • In-stock
      1-Cbz-azetidine-3-carboxylic acid|CS-W004868
      97628-92-7
    • null|null
      18107-18-1
    • ~98%
    • In-stock
      Methyl 1-Cbz-azetidine-3-carboxylate|CS-0028270
      757239-60-4

    References

    • MERCK SHARP and DOHME LIMITED Patent: WO2004/78750 A1, 2004 ; Location in patent: Page 81 ; WO 2004/078750 A1

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   55.84
  • LogP   1.428
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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