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CS-W001157 4
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N-Bocamino-cyano-acetic acid ethyl ester

  • CAS No. 865370-16-7

  • Cat. No. CS-0035554
  • Purity≥97%
  • MDL No.None

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

N-Bocamino-cyano-acetic acid ethyl ester|CS-0035554

Structure of 865370-16-7

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General Information

  • CAS No. 865370-16-7
  • Cat. No. CS-0035554
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆N₂O₄
  • Molecular Weight 228.25
  • Synonym(s) tert-butyl(ethoxycarbonyl)(cyano)methylcarbamate
  • SMILES CCOC(=O)C(C#N)N=C(O)OC(C)(C)C

Description

N-Bocamino-cyano-acetic acid ethyl ester features a protected amine and dual reactive handles—cyano and ester—enabling direct incorporation into peptide backbones or conjugation workflows. The Boc group ensures stability during synthetic manipulations, while the ethyl ester facilitates selective hydrolysis or coupling under mild conditions. This derivative serves as a key building block for non-natural amino acids and bioconjugates in medicinal chemistry.

Application

N-Bocamino-cyano-acetic acid ethyl ester serves as a versatile building block for the synthesis of cyano-containing heterocycles and amino acid derivatives. Its stability under standard reaction conditions, combined with orthogonal functional group compatibility, enables efficient incorporation into peptide-like scaffolds and pharmaceutical intermediates via nucleophilic addition, cyclization, or palladium-catalyzed coupling processes.

Synthesis

  • Route1

    References

    • Poulsen, Thomas B.; Dickmeiss, Gustav; Overgaard, Jacob; Jorgensen, Karl Anker Angewandte Chemie - International Edition, 2008 , vol. 47, # 25 p. 4687 - 4690
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      N-Bocamino-cyano-acetic acid ethyl ester|CS-0035554
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    References

    • Armstrong, Alan; Edmonds, Ian D.; Swarbrick, Martin E.; Treweeke, Nigel R. Tetrahedron, 2005 , vol. 61, # 35 p. 8423 - 8442
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    References

    • He, Xinhua; Wang, Lili; Zheng, Zhibing; Xiao, Junhai; Zhong, Wu; Li, Song Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 1 p. 553 - 557

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   91.91
  • LogP   1.17078
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   3

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