1663-47-4

Basic information

• Product Name: methyl (S)-2,5-dioxooxazolidine-4-propionate
• Synonyms: 3-[(4S)-2,5-Dioxooxazolidine-4-yl]propionic acid methyl ester;3-[(S)-2,5-Dioxooxazolidine-4-yl]propionic acid methyl ester;γ-Methyl-L-glutamate-N-carboxylic acid anhydride;Einecs 216-770-8;(S)-Methyl 3-(2,5-dioxooxazolidin-4-yl)propanoate;methyl (S)-2,5-dioxooxazolidine-4-propionate;H-GLU(OME)-NCA;Glutamic acid, 5-methyl ester, NCA
• CAS NO: 1663-47-4
• Molecular Formula: C₇H₉NO₅
• Molecular Weight: 187.15006
• EINECS: 216-770-8
• Product Categories: AMINOACIDS DERIVATIVES
• Mol File: 1663-47-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 98-99 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.31g/cm³
• Refractive Index: 1.463
• PKA: 8.87±0.40(Predicted)
• CAS DataBase Reference: methyl (S)-2,5-dioxooxazolidine-4-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-2,5-dioxooxazolidine-4-propionate(1663-47-4)
• EPA Substance Registry System: methyl (S)-2,5-dioxooxazolidine-4-propionate(1663-47-4)

Safety Data

• Hazardous Substances Data: 1663-47-4(Hazardous Substances Data)

Usage

Description

Methyl (S)-2,5-dioxooxazolidine-4-propionate is a chiral chemical compound with the molecular formula C6H9NO5. It is a derivative of oxazolidine-4-propionate, an intermediate used in the synthesis of various bioactive compounds. As a chiral molecule, it possesses a non-superimposable mirror image, and the (S) prefix in its name signifies its specific stereochemical configuration. methyl (S)-2,5-dioxooxazolidine-4-propionate plays a crucial role as an important building block in the pharmaceutical industry for the synthesis of novel compounds with potential therapeutic effects.

Uses

Used in Pharmaceutical Industry:
Methyl (S)-2,5-dioxooxazolidine-4-propionate is utilized as a key intermediate in the synthesis of various drugs and biologically-active substances. Its unique stereochemistry and structural features make it a valuable component in the development of new pharmaceuticals with improved efficacy and selectivity.
Used in Drug Synthesis:
Methyl (S)-2,5-dioxooxazolidine-4-propionate serves as a crucial building block for the creation of novel compounds with potential therapeutic effects. Its incorporation into drug molecules can enhance their pharmacological properties, leading to the discovery of new treatments for various diseases and conditions.
Used in Chiral Synthesis:
Due to its chiral nature, methyl (S)-2,5-dioxooxazolidine-4-propionate is employed in chiral synthesis, where the stereochemistry of a compound plays a significant role in its biological activity. methyl (S)-2,5-dioxooxazolidine-4-propionate can be used to create enantiomerically pure drugs, ensuring optimal therapeutic effects and minimizing potential side effects associated with the less active enantiomer.

InChI:InChI=1/C7H9NO5/c1-12-5(9)3-2-4-6(10)13-7(11)8-4/h4H,2-3H2,1H3,(H,8,11)/t4-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 503-38-8 trichloromethyl chloroformate 
• 56-86-0 L-glutamic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 67-56-1 methanol 
• 27025-22-5 D-glutamic acid-5-methyl ester; hydrochloride 

Downstream Products

• 54745-18-5 3-[(S)-3-(2-nitro-phenylsulfanyl)-2,5-dioxo-oxazolidin-4-yl]-propionic acid methyl ester 
• 70830-50-1 (S)-methyl 4,5-diamino-5-oxopentanoate 

Relevant articles and documents

-

-

Using hydrogen-bonding interactions to control the peptide secondary structures and miscibility behavior of poly(l -glutamate)s with phenolic resin

We synthesized three low-molecular-weight poly(glutamate)s-poly(γ- methyl l-glutamate) (PMLG), poly(γ-ethyl l-glutamate) (PELG), and poly(γ-benzyl l-glutamate) (PBLG)-through living ring-opening polymerization of their α-amino acid-N-carboxyanhydride derivatives and then blended them with phenolic resin to control the secondary structures of these polypeptides. Each of the three binary blends exhibited a single glass transition temperature (differential scanning calorimetry) and a single-exponential decay of proton spin-lattice relaxation times in the rotating frame [T1ρH; solid state nuclear magnetic resonance (NMR) spectroscopy], characteristic of a miscible system. The strength of the interassociative interactions depended on the nature of the hydrogen bond acceptor groups, increasing in the order phenolic/PELG > phenolic/PMLG > phenolic/PBLG, as evidenced through analyses using Fourier transform infrared (FTIR) spectroscopy and the Painter-Coleman association model. The fractions of α-helical conformations (measured using FTIR and solid-state NMR spectroscopy) of PMLG and PELG decreased initially upon increasing the phenolic content but increased thereafter; in contrast, the fraction of α-helical conformations of PBLG increased continuously upon increasing the phenolic contents. Using variable-temperature infrared spectroscopy to investigate the changes in the conformations of the secondary structures of the peptide segments in these three binary blends, we found that the α-helical conformation in these three blend systems correlated strongly with the rigidity of side-chain groups, the strength of the intermolecular hydrogen bonding with the phenolic resin, the compositions of phenolic resin, and the temperature. More interestingly, the content of α-helical conformations of the polypeptides in these phenolic/PBLG blends increased upon increasing the temperature.

PROCESS FOR THE PREPARATION OF N-CARBOXYANHYDRIDES

The invention relates to a process for the preparation of N-carboxyanhydrides by reaction of the corresponding amino acid with phosgene, diphosgene and/or triphosgene in a solvent medium, characterized in that the reaction is a least partially carried out in the presence of an unsaturated organic compound which has one or more ethylenic double bonds. The N-carboxyanhydrides are thus obtained with better yields and an improved purity.