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Boc-3-amino-2,2-dimethyl-propionic acid

  • CAS No. 180181-02-6

  • Cat. No. CS-0139511
  • Purity≥97%
  • MDL No.MFCD09952625

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

Boc-3-amino-2,2-dimethyl-propionic acid|CS-0139511

Structure of 180181-02-6

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General Information

  • CAS No. 180181-02-6
  • Cat. No. CS-0139511
  • Purity ≥97%
  • MDL No. MFCD09952625
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₄
  • Molecular Weight 217.26
  • Synonym(s) 3-((tert-Butoxycarbonyl)amino)-2,2-dimethylpropanoic acid
  • SMILES O=C(O)C(C)(C)CNC(OC(C)(C)C)=O

Description

Boc-3-amino-2,2-dimethyl-propionic acid delivers a sterically hindered, bench-stable amino acid derivative ideal for peptide synthesis. The Boc group enables efficient protection of the primary amine, while the dimethyl-substituted propionic backbone enhances solubility and reduces racemization risk during coupling. This building block integrates seamlessly into complex sequences where steric bulk and stability are critical.

Application

Boc-3-amino-2,2-dimethyl-propionic acid serves as a stable, bench-ready building block for peptide synthesis and medicinal chemistry applications. The tert-butoxycarbonyl (Boc) group provides reliable protection of the primary amine, enabling orthogonal deprotection in standard protocols. Its sterically hindered dimethyl-substituted backbone enhances stability against racemization and facilitates efficient coupling reactions with minimal epimerization. This compound functions effectively in solid-phase and solution-phase syntheses, offering high purity and consistent performance in the construction of complex peptide architectures and heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • ZALICUS PHARMACEUTICALS LTD .; PAJOUHESH , Hassan; ZHU, Yongbao; ZHOU, Yuanxi; GRIMWOOD, Mike; SIMONSON, Eric Patent: WO2011/32291 A1, 2011 ; Location in patent: Page/Page column 47 ; WO 2011/032291 A1
  • Route2
    • Methyl 3-((tert-butoxycarbonyl)amino)-2,2-dimethylpropanoate|CS-0722014
      195387-08-7
    • ~97%
    • In-stock
      Boc-3-amino-2,2-dimethyl-propionic acid|CS-0139511
      180181-02-6

    References

    • McCubbin, J. Adam; Maddess, Matthew L.; Lautens, Mark Organic Letters, 2006 , vol. 8, # 14 p. 2993 - 2996
  • Route3

    References

    • EP1548024 A1, ; Page/Page column 89-90 ;

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
Precautionary Statements : P264-P270-P301+P310-P330-P501

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   1.6219
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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