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CS-W001157 4
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(R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid

  • CAS No. 884512-77-0

  • Cat. No. CS-W006824
  • Molecule weight231.25
  • Purity≥96%
  • MDL No.MFCD09260604

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

(R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid|CS-W006824

Structure of 884512-77-0

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General Information

  • CAS No. 884512-77-0
  • Cat. No. CS-W006824
  • Purity ≥96%
  • MDL No. MFCD09260604
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₇NO₅
  • Molecular Weight 231.25
  • Synonym(s) (R)-N-Boc-2-morpholinecarboxylic acid
  • SMILES O=C([C@H]1CN(C(OC(C)(C)C)=O)CCO1)O

Description

(R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid features a stereodefined morpholine core with a robust tert-butoxycarbonyl protecting group, enabling stable incorporation into peptide synthesis workflows. This chiral building block facilitates efficient access to bioactive scaffolds through orthogonal deprotection strategies.

Application

(R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid serves as a stable, bench-ready building block for the synthesis of chiral morpholine-containing scaffolds. Its protected carboxylic acid and stereogenic center enable selective derivatization in peptide coupling and heterocycle formation. The tert-butyl carbamate group provides orthogonal protection, facilitating sequential functionalization in complex molecule assembly. This intermediate is particularly useful in medicinal chemistry campaigns targeting bioactive compounds requiring controlled stereochemistry and modifiable side chains.

Synthesis

  • Route1

    References

    • SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC. Patent: WO2008/124575 A1, 2008 ; Location in patent: Page/Page column 112; 114 ; WO 2008/124575 A1
  • Route2
    • 4-(tert-Butyl) 2-ethyl (r)-morpholine-2,4-dicarboxylate|CS-0679289
      941710-15-2
    • ~98%
    • In-stock
      (R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid|CS-W006824
      884512-77-0

    References

    • MERCK and CO., INC. Patent: WO2007/67511 A2, 2007 ; Location in patent: Page/Page column 28-29 ; WO 2007/067511 A2
  • Route3
    • (R)-2-((benzyloxy)methyl)morpholine|CS-0444962
      135065-70-2
    • ~%
    • In-stock
      (R)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid|CS-W006824
      884512-77-0

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 16 p. 4836 - 4843

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   76.07
  • LogP   0.7069
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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