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CS-W001157 4
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(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate

  • CAS No. 113850-76-3

  • Cat. No. CS-0099109
  • Purity≥98%
  • MDL No.MFCD07366813

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

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate|CS-0099109

Structure of 113850-76-3

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General Information

  • CAS No. 113850-76-3
  • Cat. No. CS-0099109
  • Purity ≥98%
  • MDL No. MFCD07366813
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₀INO₄
  • Molecular Weight 405.23
  • Synonym(s) METHYL (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-IODOPHENYL)PROPANOATE
  • SMILES O=C([C@H](CC1=CC=C(C=C1)I)NC(OC(C)(C)C)=O)OC

Description

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate is a chiral building block featuring a protected amino group and a para-iodinated phenyl moiety. This stable, bench-ready intermediate facilitates efficient coupling reactions in peptide synthesis and late-stage functionalization. The tert-butyl carbamate handle enables selective deprotection, while the iodine substituent supports palladium-catalyzed cross-couplings.

Application

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate serves as a key chiral building block for the synthesis of biologically relevant peptidomimetics and heterocyclic scaffolds. The protected amine and iodophenyl groups enable orthogonal functionalization—facilitating palladium-catalyzed cross-coupling reactions and subsequent deprotection under mild conditions. Bench-stable and readily purified by flash chromatography, it supports efficient access to complex molecular architectures in medicinal chemistry campaigns.

Synthesis

  • Route1
    • 2-((tert-Butoxycarbonyl)amino)-3-(4-iodophenyl)propanoic acid|CS-0612275
      103882-09-3
    • null|null
      74-88-4
    • ~96%
    • In-stock
      (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate|CS-0099109
      113850-76-3

    References

    • Synlett, , # 20 art. no. G30610ST, p. 3081 - 3085
  • Route2
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • Methyl 4-iodo-L-phenylalaninate|CS-0135566
      113850-77-4
    • ~%
    • In-stock
      (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate|CS-0099109
      113850-76-3

    References

    • Journal of the American Chemical Society, , vol. 114, # 19 p. 7597 - 7598
  • Route3
    • L-Phenylalanine Aspartame Impurity|CS-0229723
      63-91-2
    • ~%
    • In-stock
      (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate|CS-0099109
      113850-76-3

    References

    • Journal of Organic Chemistry, , vol. 59, # 15 p. 4206 - 4210

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-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   2.9
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   4

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