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tert-Butyl 6-aminocaproate

  • CAS No. 5514-98-7

  • Cat. No. CS-B1584
  • Purity≥95%
  • MDL No.MFCD12804788

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

tert-Butyl 6-aminocaproate|CS-B1584

Structure of 5514-98-7

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General Information

  • CAS No. 5514-98-7
  • Cat. No. CS-B1584
  • Purity ≥95%
  • MDL No. MFCD12804788
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₂₁NO₂
  • Molecular Weight 187.28
  • Synonym(s) Tert-butyl 6-aminohexanoate
  • SMILES O=C(OC(C)(C)C)CCCCCN

Description

tert-Butyl 6-aminocaproate features a protected amine group flanked by a hydrophobic tert-butyl ester, enabling stable incorporation into peptide backbones. This bench-stable derivative simplifies purification and facilitates sequential coupling in synthetic routes toward cyclic peptides and macrocyclic scaffolds.

Application

tert-Butyl 6-aminocaproate serves as a versatile bifunctional building block in peptide and macrocyclic synthesis, enabling straightforward access to lysine-derived scaffolds. The primary amine facilitates conjugation reactions, while the ester group supports orthogonal deprotection and derivatization. Its tert-butyl protection offers excellent bench stability and compatibility with standard coupling protocols, simplifying purification and downstream functionalization in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Lampe, Thomas; Kast, Raimund; Beck, Hartmut; Stoll, Friederike; Becker, Eva-Maria; Jeske, Mario; Schuhmacher, Joachim Patent: US2010/261736 A1, 2010 ; Location in patent: Page/Page column 31 ;
  • Route2

    References

    • Schmuck, Carsten; Rehm, Thomas; Geiger, Lars; Schaefer, Mathias Journal of Organic Chemistry, 2007 , vol. 72, # 16 p. 6162 - 6170
  • Route3

    References

    • Schmuck, Carsten; Rehm, Thomas; Geiger, Lars; Schaefer, Mathias Journal of Organic Chemistry, 2007 , vol. 72, # 16 p. 6162 - 6170

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   52.32
  • LogP   1.8472
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   5

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