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tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate

  • CAS No. 145149-48-0

  • Cat. No. CS-W002775
  • Molecule weight251.32
  • Purity≥97%
  • MDL No.MFCD01457313

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

tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate|CS-W002775

Structure of 145149-48-0

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General Information

  • CAS No. 145149-48-0
  • Cat. No. CS-W002775
  • Purity ≥97%
  • MDL No. MFCD01457313
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₁NO₃
  • Molecular Weight 251.32
  • Synonym(s) N-Boc-DL-phenylalaninol
  • SMILES O=C(OC(C)(C)C)NC(CO)CC1=CC=CC=C1

Description

tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate features a hydroxyl-bearing chiral center flanked by a phenyl group and a tert-butyl carbamate protecting group, offering robust stability under standard conditions. This scaffold integrates readily into synthetic sequences requiring orthogonal protection strategies, particularly in peptide and complex organic syntheses where moisture-tolerant handling is essential.

Application

tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate serves as a stable, bench-ready precursor for the synthesis of chiral β-hydroxy amino acid derivatives. The protected hydroxyl and amine functionalities enable orthogonal manipulation in peptide and heterocyclic synthesis. It functions effectively in standard coupling and reduction protocols, offering reliable access to pharmacologically relevant scaffolds with high functional group tolerance and straightforward purification.

Synthesis

  • Route1

    References

    • Takasago International Corporation Patent: EP2141142 A1, 2010 ; Location in patent: Page/Page column 16 ;
  • Route2

    References

    • Chong, Hyun-Soon; Song, Hyun A.; Dadwal, Mamta; Sun, Xiang; Sin, Inseok; Chen, Yunwei Journal of Organic Chemistry, 2010 , vol. 75, # 1 p. 219 - 221
  • Route3
    • 2-(tert-Butoxycarbonylamino)-3-phenylpropanoic acid Bortezomib Impurity|CS-0169689
      4530-18-1
    • null|null
      541-41-3
    • ~%
    • tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate|CS-W002775
      145149-48-0

    References

    • US2006/46978 A1, ; Page/Page column 12 ; US 20060046978 A1

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   58.56
  • LogP   2.1147
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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