129288-34-2

Usage

Chemical Family

The compound belongs to the oxazolidinedione family.

Chirality

The compound is chiral, with a specific stereochemistry denoted by the (S)in its name, indicating that it is the S enantiomer.

Usage

The compound is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals.

Versatility

The compound's unique structure and functional groups make it a versatile intermediate in organic synthesis, allowing for the creation of diverse molecules with a wide range of biological activities.

Stability and Reactivity

The presence of the 1,1-dimethylethoxy and phenyl groups in the compound's structure contribute to its stability and reactivity in chemical reactions.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 47375-34-8 Boc-Tyr(t-Bu)-OH 

Downstream Products

• 129288-46-6 (S)-4-(4-tert-Butoxy-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis of α-Amino Acid N-Carboxyanhydrides

A simple phosgene- and halogen-free method for synthesizing α-amino acid N-carboxyanhydrides (NCAs) is described. The reaction between Boc-protected α-amino acids and T3P reagent gave the corresponding NCA derivatives in good yield and purity with no detectable epimerization. The process is safe, is easy-to-operate, and does not require any specific installation. It generates nontoxic, easy to remove byproducts. It can apply to the preparation of NCAs for the on-demand on-site production of either little or large quantities.

METHOD OF SYNTHESIZING N-CARBOXYANHYDRIDE USING FLOW REACTOR

PROBLEM TO BE SOLVED: To provide a synthesis method that allows high-yield continuous production of a compound of interest in synthesis and production of N-carboxyanhydride (NCA) and the like using a flow reactor. SOLUTION: In a synthesis method using a flow reactor 100, a basic solution adjusted in advance to a pH of 7-14 becomes acidic with a pH of 0-7, or an acidic solution adjusted in advance to a pH of 0-7 becomes basic with a pH of 7-14, within 60 seconds after the start of mixture of at least two ingredient solutions. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor

Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.