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CS-W001157 4
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(αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid

  • CAS No. 33125-05-2

  • Cat. No. CS-W020686
  • Purity≥98%
  • MDL No.MFCD00062043

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

(αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid|CS-W020686

Structure of 33125-05-2

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General Information

  • CAS No. 33125-05-2
  • Cat. No. CS-W020686
  • Purity ≥98%
  • MDL No. MFCD00062043
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇NO₄
  • Molecular Weight None
  • Synonym(s) (2R)-2-(tert-Butoxycarbonylamino)-2-phenylethanoic acid; (R)-2-((tert-Butoxycarbonyl)amino)-2-phenylacetic acid; (R)-2-[(tert-Butoxycarbonyl)amino]-2-phenylacetic acid
  • SMILES OC([C@H](NC(OC(C)(C)C)=O)C1=CC=CC=C1)=O

Description

This bench-stable, moisture-tolerant chiral building block features a protected α-amino acid scaffold with a stereodefined (αR) configuration. The tert-butoxycarbonyl (Boc) group enables straightforward deprotection under mild acidic conditions, while the para-substituted aryl moiety supports efficient coupling reactions in peptide synthesis and medicinal chemistry applications.

Application

(αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid serves as a chiral building block for synthesizing β-amino acid derivatives and peptidomimetics. Its (αR) configuration enables stereocontrolled coupling reactions, while the tert-butoxycarbonyl (Boc) group provides robust protection of the amine under acidic conditions. The compound exhibits excellent bench stability, facilitates straightforward purification, and functions reliably in standard peptide coupling protocols.

Synthesis

  • Route1
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • H-D-Phg-OH Ampicillin Impurity|CS-0229771
      875-74-1
    • ~99%
    • In-stock
      (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid|CS-W020686
      33125-05-2

    References

    • Skerlj, Renato; Bridger, Gary; Zhou, Yuanxi; Bourque, Elyse; McEachern, Ernest; Metz, Markus; Harwig, Curtis; Li, Tong-Shuang; Yang, Wen; Bogucki, David; Zhu, Yongbao; Langille, Jonathan; Veale, Duane; Ba, Tuya; Bey, Michael; Baird, Ian; Kaller, Alan; Krumpak, Maria; Leitch, David; Satori, Michael; Vocadlo, Krystyna; Guay, Danielle; Nan, Susan; Yee, Helen; Crawford, Jason; Chen, Gang; Wilson, Trevor; Carpenter, Bryon; Gauthier, David; MacFarland, Ron; Mosi, Renee; Bodart, Veronique; Wong, Rebecca; Fricker, Simon; Schols, Dominique Journal of Medicinal Chemistry, 2013 , vol. 56, # 20 p. 8049 - 8065
  • Route2

    References

    • Chakraborty, Tushar K.; Ghosh, Animesh Tetrahedron Letters, 2002 , vol. 43, # 52 p. 9691 - 9693
  • Route3
    • null|null
      762-75-4
    • H-D-Phg-OH Ampicillin Impurity|CS-0229771
      875-74-1
    • ~%
    • In-stock
      (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid|CS-W020686
      33125-05-2

    References

    • European Journal of Medicinal Chemistry, , vol. 63, p. 231 - 238

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   75.63
  • LogP   2.337
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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