104324-16-5

Basic information

• Product Name: (N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE
• Synonyms: (N-CHLOROACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE;(N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE;(S)-4-BENZYL-3-CHLOROACETYL-2-OXAZOLIDINONE;(S)-4-BENZYL-3-CHLOROACETYL-2-OXAZOLIDIN;(N-Chloracetyl)-(R)-4-benzyl-2-oxazolidinone;(N-Chloracetyl)-(S)-4-benzyl-2-oxazolidinone;(S)-4-Benzyl-3-(2-chloroacetyl)oxazolidin-2-one;(S)-4-Benzyl-3-chloroacetyl-2-oxazolidinone,99%e.e.
• CAS NO: 104324-16-5
• Molecular Formula: C₁₂H₁₂ClNO₃
• Molecular Weight: 253.68
• Product Categories: Peptide
• Mol File: 104324-16-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 78-82 °C(lit.)
• Boiling Point: 416.2°Cat760mmHg
• Flash Point: 205.5°C
• Appearance: /
• Density: 1.347g/cm³
• Vapor Pressure: 3.88E-07mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.49±0.40(Predicted)
• CAS DataBase Reference: (N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE(104324-16-5)
• EPA Substance Registry System: (N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE(104324-16-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 104324-16-5(Hazardous Substances Data)

Usage

Description

(N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE is a chemical compound widely utilized in the field of organic chemistry. It features a benzyl group, known for its stability and ease of removal, making it a valuable component in organic synthesis. Additionally, the presence of an oxazolidinone moiety, commonly found in antibiotics such as linezolid and eperezolid, contributes to its potential applications in pharmaceutical chemistry. The N-chloroacetyl component endows the molecule with reactivity due to the presence of a good leaving group, allowing for versatile reactions in the synthesis of complex compounds. Due to its reactivity and potential hazards, careful handling of this compound is essential.

Uses

Used in Organic Synthesis:
(N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE is used as an intermediate in organic synthesis for its stability and ease of removal, facilitating the construction of complex organic molecules.
Used in Pharmaceutical Chemistry:
In the Pharmaceutical Industry, (N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE is used as a building block for the development of new antibiotics, leveraging the oxazolidinone moiety's known antibiotic properties.
Used in the Synthesis of Complex Compounds:
(N-CHLOROACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE is used as a reactive intermediate for the synthesis of complex compounds, taking advantage of the reactivity of the N-chloroacetyl group and its good leaving group properties.

InChI:InChI=1/C12H12ClNO3/c13-7-11(15)14-10(8-17-12(14)16)6-9-4-2-1-3-5-9/h1-5,10H,6-8H2/t10-/m0/s1

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 218439-10-2 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane 
• 1361955-15-8 C₁₃H₁₃NO₃S₂ 
• 1361955-33-0 (4S)-3-[(2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone 
• 1361955-27-2 (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone 
• 1089174-11-7 (4S,2'S,3'R,6'R,7'S)-(+)-3-[9'-(tert-butyldiphenylsilyloxy)-2'-chloro-3'-hydroxy-6',7'-O-isopropylidenenonanoyl]-4-benzyloxazolidinone 
• 1089174-15-1 (4S,2'S,3'R,6'S,7'S)-(-)-3-[9'-(tert-butyldiphenylsilyloxy)-2'-chloro-3'-hydroxy-6',7'-O-isopropylidenenonanoyl]-4-benzyloxazolidinone 
• 104418-82-8 (4S)-3-((4'S,5'R)-5'-((1S,3E)-1-methyl-3-pentenyl)-2'-thioxo-4'-oxazolidinylcarbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104324-19-8 (4S)-3-((4'S,5'R)-5'-((1R,3E)-1-methyl-3-pentenyl)-2'-thioxo-4'-oxazolidinylcarbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104324-20-1 (S)-4-Benzyl-3-[(4S,5R)-5-((E)-pent-3-enyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one 
• 104324-21-2 (S)-4-Benzyl-3-((4S,5R)-5-isopropyl-2-thioxo-oxazolidine-4-carbonyl)-oxazolidin-2-one 
• 104324-22-3 (4S)-3-<((4'S,5'R)-5'-methyl-2'-thioxo-4'-oxazolidinyl)carbonyl>-4-(phenylmethyl)-2-oxazolidinone 
• 104324-18-7 (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone 

Relevant articles and documents

Synthesis and characterization of novel chiral imidazolium and pyridinium ionic liquids derived from tartaric acid and 2-oxazolidinone

Novel chiral imidazolium and pyridinium ionic liquids based on tartaric acid and 2-oxazolidinone were designed. Symmetrical dicationic ionic liquids based on tartaric acid have been synthesized and characterized. These chiral ionic liquids were designed b

Stereoselective Visible-Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal-free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light-driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2-trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D-printed mesoreactor, without any change in the diastereoseletctivity of the process.

PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES

Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.