(R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Name: (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 364077-84-9
Cat. No. CS-M1683
Purity≥96%
MDL No.MFCD06409980

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid|CS-M1683

Structure of 364077-84-9

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General Information

CAS No. 364077-84-9
Cat. No. CS-M1683
Purity ≥96%
MDL No. MFCD06409980
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₅NO₅
Molecular Weight 229.23
Synonym(s) N-Boc-4-oxo-D-proline Methyl ester
SMILES CC(C)(OC(N1CC(C[C@@H]1C(O)=O)=O)=O)C

Description

This chiral pyrrolidine derivative features a protected amine and a ketone at the C4 position, enabling direct incorporation into peptide synthesis. The tert-butoxycarbonyl group provides stability and orthogonal deprotection compatibility. This scaffold supports efficient access to bioactive cyclic peptides and constrained peptidomimetics through modular derivatization.

Application

(R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid serves as a versatile chiral building block in synthetic organic chemistry, enabling the construction of pyrrolidine-based scaffolds prevalent in medicinal chemistry. The protected amine and ketone functionalities offer orthogonal reactivity, facilitating selective transformations and downstream derivatization. Its bench-stable nature and compatibility with standard coupling and reduction protocols make it well-suited for iterative synthesis and scale-up applications.

Synthesis

Route1
- In-stock
  
  135042-12-5
- ~97%
- In-stock
  
  364077-84-9
References
- Van Huis, Chad A.; Casimiro-Garcia, Agustin; Bigge, Christopher F.; Cody, Wayne L.; Dudley, Danette A.; Filipski, Kevin J.; Heemstra, Ronald J.; Kohrt, Jeffrey T.; Leadley Jr., Robert J.; Narasimhan, Lakshmi S.; McClanahan, Thomas; Mochalkin, Igor; Pamment, Michael; Thomas Peterson; Sahasrabudhe, Vaishali; Schaum, Robert P.; Edmunds, Jeremy J. Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 6 p. 2501 - 2511

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 83.91
LogP 0.6495
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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(R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

CAS No. 364077-84-9

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