(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid

Name: (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid
Brand: ChemScene
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CAS No. 192315-36-9
Cat. No. CS-0449181
Molecule weight315.75
Purity≥98%
MDL No.MFCD02682260

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(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid|CS-0449181

Structure of 192315-36-9

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General Information

CAS No. 192315-36-9
Cat. No. CS-0449181
Purity ≥98%
MDL No. MFCD02682260
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈ClNO₅
Molecular Weight 315.75
Synonym(s) Boc-Tyr(3-Cl)-OH·DCHA
SMILES CC(C)(OC(N[C@H](C(O)=O)CC1=CC(Cl)=C(O)C=C1)=O)C

Description

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid is a chiral building block featuring a protected amine and a phenolic hydroxyl group. This configuration enables selective conjugation in peptide synthesis, while the electron-withdrawing chlorine enhances reactivity in downstream functionalization. The tert-butyl carbamate moiety provides stability under basic conditions and facilitates orthogonal deprotection.

Application

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid serves as a key chiral building block for the synthesis of bioactive molecules, particularly in the development of β-amino acid derivatives and peptidomimetics. The protected amine and phenolic hydroxyl groups enable orthogonal functionalization, while the tert-butyl carbamate moiety provides excellent bench stability and ease of purification. This compound facilitates efficient coupling reactions and is well-suited for iterative synthetic sequences in medicinal chemistry workflows.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 95.86
LogP 2.566
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Tyrosine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid

CAS No. 192315-36-9

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