Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

Name: Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate
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CAS No. 225517-15-7
Cat. No. CS-0513839
Purity≥95%
MDL No.None

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Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate|CS-0513839

Structure of 225517-15-7

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General Information

CAS No. 225517-15-7
Cat. No. CS-0513839
Purity ≥95%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉NO₅
Molecular Weight 281.30
Synonym(s) (S)-Methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate
SMILES CC(C)(C)OC(N[C@@H](C1=CC=C(C=C1)O)C(OC)=O)=O

Description

Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate features a chiral α-amino acid scaffold with a protected amine and a phenolic hydroxyl group. This bifunctional intermediate integrates readily into peptide synthesis workflows, where the tert-butyl carbamate moiety enables orthogonal protection. The pendant hydroxyl supports further derivatization, while the methyl ester facilitates selective transformation under standard conditions.

Application

Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate serves as a key chiral building block for synthesizing pharmaceutically relevant β-amino alcohol scaffolds. The molecule combines a protected α-amino acid functionality with a phenolic handle, enabling selective derivatization and orthogonal deprotection sequences. Its bench-stable tert-butyl carbamate group facilitates efficient peptide coupling and solid-phase synthesis workflows, while the methyl ester supports late-stage functionalization. This compound enables reliable access to complex heterocyclic motifs through established cyclization protocols.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 84.86
LogP 2.131
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

CAS No. 225517-15-7

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