(S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER（CAS# 91229-91-3)
Introduction
di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate is a compound whose chemical formula is C14H23NO6. The following is a description of the properties, uses, preparation and safety information of the compound:
Nature:
-Appearance: di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate is a colorless to white crystalline solid.
-Solubility: It is soluble in organic solvents such as ethanol, methanol and dimethyl sulfoxide.
-Melting point: The compound melts at about 104-105°C.
Use:
di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate is a commonly used amino acid derivative, often used as a reagent in organic synthesis. It can be used to synthesize biologically active compounds, such as drugs and polymer materials.
Method:
The preparation of di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate is usually carried out by the following steps:
1. Dissolve pyroglutamic acid tert-butyl ester in dry dimethyl sulfoxide.
2. An appropriate amount of N,N'-dihydroxyethyl isopropanamide was added and the reaction mixture was cooled to below 0°C.
3. Add di-tert-butyl carbonate slowly while maintaining the temperature of the reaction mixture below 0°C.
4. After completion of the reaction, the reaction mixture was added to water to produce a solid precipitate of di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate.
5. The final product was obtained by the steps of crystallization, filtration and drying.
Safety Information:
di-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate should be used and handled in accordance with safe practices to avoid exposure to skin, eyes and inhalation. In addition, it should be stored in a dry, cool place and away from fire and oxidants. For specific safety information, refer to the Chemical Safety Data Sheet (MSDS) or the relevant information provided by the supplier.
Application
(S)-N-alpha-t-Butyloxycarbonyl-pyroglutamic acid t-butyl ester (Boc-Pyr-OtBu, CAS 91229-91-3) is a protected, chiral derivative of L-pyroglutamic acid. It features an acid-labile tert-butyl ester (OtBu) protecting the C-terminus and a base-stable tert-butyloxycarbonyl (Boc) group protecting the N-terminus. As a versatile building block, it serves as a key pharmaceutical intermediate in peptide synthesis and drug discovery.
In medicinal chemistry, Boc-Pyr-OtBu is a critical starting material for constructing conformationally constrained peptidomimetics. Its rigid pyroglutamic acid core facilitates the stereoselective synthesis of complex peptides and bioactive compounds. Researchers utilize it to synthesize enantiopure azabicycloalkane amino acids, which are valuable for mimicking different peptide conformations in drug design. High-purity (>98%) Boc-Pyr-OtBu ensures reproducible results in custom chemical synthesis and GMP manufacturing. Xinchem offers custom synthesis, custom chemical synthesis, and contract manufacturing of this essential chiral building block to support your pharmaceutical research and development. Contact us for a competitive quote and reliable global supply.
