Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate

Name: Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate
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CAS No. 328086-60-8
Cat. No. CS-0139871
Molecule weight286.33
Purity≥97%
MDL No.MFCD28138267

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Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate|CS-0139871

Structure of 328086-60-8

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General Information

CAS No. 328086-60-8
Cat. No. CS-0139871
Purity ≥97%
MDL No. MFCD28138267
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₂N₂O₅
Molecular Weight 286.33
Synonym(s) Methyl (αS,3S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidinepropanoate
SMILES CC(C)(C)OC(N[C@@H](C[C@@H]1CCNC1=O)C(OC)=O)=O

Description

Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate is a chiral dipeptide building block featuring a protected α-amino group and a pyrrolidinone moiety. This configuration enables efficient coupling in peptide synthesis, offering enhanced solubility and stability under standard conditions.

Application

Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate serves as a key chiral building block for the synthesis of pyrrolidine-containing peptide mimetics and heterocyclic scaffolds. Its well-defined stereochemistry and orthogonal functionality enable reliable coupling reactions, while the tert-butyl carbamate group offers stable protection under standard conditions. The methyl ester facilitates downstream transformations, and the molecule exhibits excellent bench stability and ease of purification—ideal for iterative synthetic workflows in medicinal chemistry.

Synthesis

Route1
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References
- Yang, Syaulan; Chen, Shu-Jen; Hsu, Min-Feng; Wu, Jen-Dar; Tseng, Chien-Te K.; Liu, Yu-Fan; Chen, Hua-Chien; Kuo, Chun-Wei; Wu, Chi-Shen; Chang, Li-Wen; Chen, Wen-Chang; Liao, Shao-Ying; Chang, Teng-Yuan; Hung, Hsin-Hui; Shr, Hui-Lin; Liu, Cheng-Yuan; Huang, Yu-An; Chang, Ling-Yin; Hsu, Jen-Chi; Peters, Clarence J.; Wang, Andrew H.-J.; Hsu, Ming-Chu Journal of Medicinal Chemistry, 2006 , vol. 49, # 16 p. 4971 - 4980

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

Quality Control

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Computational Chemistry Data

TPSA 93.73
LogP 0.5789
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids C-ProtectedAmino Acids

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-((S)-2-oxopyrrolidin-3-yl)propanoate

CAS No. 328086-60-8

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