583-47-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxazolidine-2,5-dione is used as a key intermediate in the synthesis of various pharmaceuticals. Its ability to undergo ring opening and acylation reactions allows for the creation of diverse drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-benzyloxazolidine-2,5-dione serves as a crucial building block for the development of new agrochemicals. Its reactivity and versatility enable the synthesis of compounds with pesticidal properties, contributing to the advancement of crop protection strategies.
Used in Organic Synthesis Research:
4-Benzyloxazolidine-2,5-dione is employed as a versatile reagent in organic synthesis research. Its unique chemical properties and reactivity make it an essential component in the development of novel synthetic pathways and the exploration of new chemical reactions.
Used in Fine Chemicals Production:
4-Benzyloxazolidine-2,5-dione is utilized in the production of various fine chemicals, including specialty chemicals and intermediates for further chemical transformations. Its presence in these applications highlights its importance in the synthesis of high-value chemical products.

InChI:InChI=1/C10H9NO3/c12-9-8(11-10(13)14-9)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,13)

Upstream product

• 75-44-5 phosgene 
• 150-30-1 Phenylalanine 
• 60-29-7 diethyl ether 
• 508220-75-5 2-azidocarbonyl-3-phenyl-propionic acid 
• 77357-58-5 2-((methoxycarbonyl)amino)-3-phenylpropanoic acid 
• 3588-57-6 Z-DL-Phe-OH 
• 79-22-1 methyl chloroformate 
• 2899-52-7 N,O-bis-(trimethylsilyl)phenylalanine 
• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 59483-84-0 bis(pentafluorophenyl)carbonate 
• 63-91-2 L-phenylalanine 
• 133565-25-0 phenylalanine, tetrabutylammonium carboxylate salt 

Downstream Products

• 15028-44-1 DL-phenylalanine methyl ester 
• 51163-51-0 phenylalanine-glycine-glycine 
• 131100-60-2 Phenylalanin-aethylamid 
• 4294-26-2 phenylalanylglycine 
• 150-30-1 Phenylalanine 
• 17193-31-6 (R,S)-2-amino-3-phenylpropionamide 
• 40689-17-6 N-(1-benzyl-2-oxo-butyl)-propionamide 
• 6330-09-2 5-benzyl-2-thiohydantoin 
• 3705-50-8 2-amino-N,N-dimethyl-3-phenylpropanamide 
• 108514-97-2 N-dimethylcarbamoyl-phenylalanine 
• 60058-40-4 2S-amino-N-methyl-3-phenylpropionamide 
• 40350-94-5 Phenylalanylchlorid-hydrochlorid 
• 92008-08-7 C₁₃H₂₀N₂O₂ 
• 14348-35-7 2-Amino-N-{2-[2-(2-amino-3-phenyl-propionylamino)-ethyldisulfanyl]-ethyl}-3-phenyl-propionamide 

Relevant academic research and scientific papers

N-carboxyl-DL-phenylalanine anhydride

The N1-H1 imino group of the five-membered ring of the title compound, C10H9NO3, forms intermolecular hydrogen bonds between O1 along the a axis and between O3 along the b axis. Thus, a two-dimensional hydrogen-bonding network forms a layer perpendicular to the c axis. The layer, which consists of one of two independent molecules, stacks alternately along the c axis and produces a sandwich structure.

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.

Synthesis of sterically hindered N-acylated amino acids from N-carboxyanhydrides

Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.

N-CARBOXY AMINO ACID ANHYDRIDE AND AMINO ACID CARBAMATE COMPOUND PRODUCTION METHOD

A method for production of an N-carboxy amino acid anhydride with efficiency is provided. The method for production of an N-carboxy amino acid anhydride includes a step of reaction of an amino acid organic salt compound with a carbonic acid diester.

PROCESS FOR PRODUCING AMINO ACID N-CARBOXYANHYDRIDE

The present invention provides a process for producing an amino acid N-carboxyanhydride, which comprises reacting an amino acid or a derivative thereof with a compound represented by the following formula (1): wherein R1 and R2 represent the same or different electron-withdrawing substituents and each independently are an optionally substituted acyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted perfluoroalkyl group, an optionally substituted perchloroalkyl group, a cyano group, a halogen atom, or a nitro group; and a and b are the same or different and each are an integer of 1-5.

A new simple and quantitative synthesis of α-aminoacid-N-carboxyanhydrides (oxazolidines-2,5-dione)

Nitrosation of chiral N-carbamoylaminoacids with a mixture of NO and O2 gives, with the same configuration and in quantitative yield the corresponding α-aminoacid-N-carboxyanhydrides (NCA), well known precursors of peptides. The by products of this reaction are N2 and H2O. Copyright (C) 1996 Elsevier Science Ltd.

THE PREPARATION OF N-CARBOXYANHYDRIDES OF α-AMINO ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE

A syntheis of the N-carboxyanhydrides (NCA's) of several α-amino acids using bis(trichloromethyl)carbonate, 1, is reported.The triphosgene is used to supply phosgene in situ in stoichiometric amounts; it is particularly effective for preparing NCA's of amino acids with long, aliphatic side chains.

ENANTIOMERIC QUANTIFICATIONS OF AMINO ACIDS THROUGH THEIR Nα-ACYL AMIDES BY GAS CHROMATOGRAPHY.

Apparent separation of 1.1 or higher on Chiralsil Val III can be obtained for Nα-acyl N-alkyl aminoacid amides allowing the use of short capillary gas chromatographic columns.A clean derivatization protocol without racemization is described, proceding through the NCA derivatives that are prepared from "in situ" silylated amino acids with trimethylsilyl cyanide.