2,5-Dioxopyrrolidin-1-yl (tert-butoxycarbonyl)-L-valinate

Name: 2,5-Dioxopyrrolidin-1-yl (tert-butoxycarbonyl)-L-valinate
Brand: ChemScene
Availability: InStock
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CAS No. 3392-12-9
Cat. No. CS-W009916
Purity≥97%
MDL No.MFCD00037906

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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2,5-Dioxopyrrolidin-1-yl (tert-butoxycarbonyl)-L-valinate|CS-W009916

Structure of 3392-12-9

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General Information

CAS No. 3392-12-9
Cat. No. CS-W009916
Purity ≥97%
MDL No. MFCD00037906
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₂N₂O₆
Molecular Weight 314.33
Synonym(s) tert-Butyl (S)-(1-(((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)-2-methylpropyl)carbamate
SMILES CC(C)[C@@H](C(ON1C(CCC1=O)=O)=O)NC(OC(C)(C)C)=O

Description

This tert-butoxycarbonyl-protected valine derivative features a reactive dioxopyrrolidinyl leaving group, enabling efficient amide bond formation under mild conditions. The bulky tert-butyl carbamate moiety provides enhanced stability and ease of purification, while the hydrophobic valine side chain supports incorporation into peptide sequences with minimal steric interference.

Application

Boc-L-valine 2,5-dioxopyrrolidin-1-yl ester serves as a robust amino acid coupling agent, enabling efficient amide bond formation in peptide synthesis. The pyrrolidinone ester moiety ensures high reactivity with primary amines under mild conditions, while the tert-butoxycarbonyl (Boc) group provides stable protection of the α-amino function. This compound exhibits excellent bench stability, simplifies purification by precipitation, and is compatible with a broad range of functional groups, making it a reliable building block for fragment assembly and synthetic peptide workflows.

Synthesis

Route1
- In-stock
  
  6066-82-6
- In-stock
  
  13734-41-3
- ~70%
- In-stock
  
  3392-12-9
References
- Cregge, Robert J.; Durham, Sherrie L.; Farr, Robert A.; Gallion, Steven L.; Hare, C. Michelle; Hoffman, Robert V.; Janusz, Michael J.; Kim, Hwa-Ok; Koehl, Jack R.; Mehdi, Shujaath; Metz, William A.; Peet, Norton P.; Pelton, John T.; Schreuder, Herman A.; Sunder, Shyam; Tardif, Chantal Journal of Medicinal Chemistry, 1998 , vol. 41, # 14 p. 2461 - 2480
Route2
- In-stock
  
  13734-41-3
- 107960-02-1
- ~93%
- In-stock
  
  3392-12-9
References
- Jaoudai, Mahmoud; Martinez, Jean; Castro, Bertrand Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2364 - 2367
Route3
- In-stock
  
  13734-41-3
- 96935-01-2
- ~10%
- In-stock
  
  3392-12-9
References
- Takeda; Ayabe; Suzuki; Konda; Harigaya Synthesis, 1991 , # 9 p. 689 - 691

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H401
Precautionary Statements : P273-P501

Quality Control

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Computational Chemistry Data

TPSA 102.01
LogP 1.1429
H_Acceptors 6
H_Donors 1
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 Valine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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2,5-Dioxopyrrolidin-1-yl (tert-butoxycarbonyl)-L-valinate

CAS No. 3392-12-9

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