(S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

Name: (S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 2873-37-2
Cat. No. CS-0154140
Molecule weight376.45
Purity≥97%
MDL No.MFCD01862400

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(S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate|CS-0154140

Structure of 2873-37-2

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General Information

CAS No. 2873-37-2
Cat. No. CS-0154140
Purity ≥97%
MDL No. MFCD01862400
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₈N₂O₅
Molecular Weight 376.45
Synonym(s) Cbz-Pro-Leu-OMe
SMILES CC(C[C@H](NC([C@@H]1CCCN1C(OCC2=CC=CC=C2)=O)=O)C(OC)=O)C

Description

(S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate is a chiral, bench-stable building block featuring a pyrrolidine core with a carbamoyl-linked ketone-bearing side chain. This configuration supports stereocontrolled synthesis in medicinal chemistry and peptide-like scaffold development, where the methoxy and methyl groups enhance solubility and modulate reactivity.

Application

(S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate serves as a chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. Its pyrrolidine core enables efficient incorporation into cyclic peptides, while the carbamoyl linkage supports orthogonal functionalization. The (S)-configured side chain provides stereochemical control in cascade cyclizations and offers bench-stable handling with predictable reactivity in standard coupling protocols.

Synthesis

Route1
- In-stock
  
  7517-19-3
- In-stock
  
  1148-11-4
- ~92%
- In-stock
  
  2873-37-2
References
- Liu, Jingyuan; West, Kevin R.; Bondy, Chantelle R.; Sanders, Jeremy K. M. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 5 p. 778 - 786
Route2
- 2666-93-5
- In-stock
  
  1148-11-4
- ~96%
- In-stock
  
  2873-37-2
References
- Pellicciari, Roberto; Garzon-Aburbeh, Aaron; Natalini, Benedetto; Marinozzi, Maura; Clerici, Carlo; et al. Journal of Medicinal Chemistry, 1993 , vol. 36, # 26 p. 4201 - 4207
Route3
- 627-36-1
- In-stock
  
  7517-19-3
- In-stock
  
  1148-11-4
- ~59%
- In-stock
  
  2873-37-2
References
- Ajinomoto Co., Inc. Patent: US3933783 A1, 1976 ;

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

Quality Control

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Computational Chemistry Data

TPSA 84.94
LogP 2.4915
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 7

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Leucine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-Benzyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

CAS No. 2873-37-2

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