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CS-W001157 4
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trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate

  • CAS No. 146307-51-9

  • Cat. No. CS-W023036
  • Purity≥97%
  • MDL No.MFCD17015041

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

trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate|CS-W023036

Structure of 146307-51-9

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General Information

  • CAS No. 146307-51-9
  • Cat. No. CS-W023036
  • Purity ≥97%
  • MDL No. MFCD17015041
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₃NO₄
  • Molecular Weight 257.33
  • Synonym(s) Methyl cis-4-(boc-amino)cyclohexanecarboxylate
  • SMILES C(C)(C)(C)OC(=O)N[C@H]1CC[C@@H](CC1)C(=O)OC

Description

trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate features a rigid, trans-configured cyclohexane core with a bench-stable Boc-protected amine and ester handle. This configuration enables selective derivatization in peptide synthesis and chiral building block applications, offering predictable stereochemical control under standard conditions.

Application

trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate serves as a stereochemically defined building block for cyclohexane-based peptidomimetics and bioactive heterocycles. The Boc-protected amine and ester functionalities offer orthogonal reactivity, enabling selective deprotection and derivatization. Its trans configuration ensures predictable conformational control in subsequent transformations, while the tert-butyl carbamate group provides excellent bench stability and ease of purification.

Synthesis

  • Route1

    References

    • Shionogi and Co., Ltd. Patent: US2010/273841 A1, 2010 ; Location in patent: Page/Page column 21 ; US 20100273841 A1
  • Route2
    • In-stock
      trans-4-Carbomethoxycyclohexane-1-carboxylic acid|CS-D1137
      15177-67-0
    • null|null
      75-65-0
    • ~%
    • In-stock
      trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate|CS-W023036
      146307-51-9

    References

    • EP1582521 A1, ; Page/Page column 116-117 ;
  • Route3
    • null|null
      600133-26-4
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~%
    • In-stock
      trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate|CS-W023036
      146307-51-9

    References

    • EP2017261 A1, ; Page/Page column 30 ;

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   64.63
  • LogP   2.2429
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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