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

General Description

(N-Chloroacetyl)-(4S)-Benzyl-2-Oxazolidinone is a chemical compound, typically used in the field of organic chemistry. It contains a benzyl group, which is often used in organic synthesis due to its stability and ease of removal. Furthermore, an oxazolidinone moiety is present, a common feature found in antibiotics such as linezolid and eperezolid. While its specific uses can greatly vary depending on the context, it often serves as an intermediate in the synthesis of other complex compounds. The N-chloroacetyl component lends the molecule reactivity due to the presence of a good leaving group. As with all chemicals, careful handling is advised due to potential risks and hazards.

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

• 126788-82-7 (S)-4-Benzyl-3-[(E)-(2S,3R,4R,5S)-2-chloro-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 104324-17-6 (4S)-(+)-3-(azidoacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 902132-64-3 C₁₅H₁₅BrClNO₄ 
• 902132-65-4 C₁₅H₁₆BrNO₄ 
• 902132-67-6 C₂₁H₃₀BrNO₄Si 
• 247146-12-9 (S)-4-Benzyl-3-((S)-3-hydroxy-4,4-dimethyl-6,6-diphenyl-hex-5-enoyl)-oxazolidin-2-one 
• 1062211-31-7 (S)-4-Benzyl-3-(2-methyleneamino-acetyl)-oxazolidin-2-one 
• 184714-55-4 N-[2-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-formamide 
• 104324-23-4 (S)-4-Benzyl-3-((4S,5R)-5-phenyl-2-thioxo-oxazolidine-4-carbonyl)-oxazolidin-2-one 
• 104324-18-7 (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104324-22-3 (4S)-3-<((4'S,5'R)-5'-methyl-2'-thioxo-4'-oxazolidinyl)carbonyl>-4-(phenylmethyl)-2-oxazolidinone 
• 104324-21-2 (S)-4-Benzyl-3-((4S,5R)-5-isopropyl-2-thioxo-oxazolidine-4-carbonyl)-oxazolidin-2-one 
• 104324-20-1 (S)-4-Benzyl-3-[(4S,5R)-5-((E)-pent-3-enyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one 
• 104324-19-8 (4S)-3-((4'S,5'R)-5'-((1R,3E)-1-methyl-3-pentenyl)-2'-thioxo-4'-oxazolidinylcarbonyl)-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.