1432-43-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Acetyl-2-oxazolidinone is used as a reagent for the enantioselective synthesis of various biologically active compounds, such as (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone. These compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
3-Acetyl-2-oxazolidinone is also a useful synthetic intermediate in the synthesis of 2-Oxazolone (O846555), which is a versatile tool for synthetic organic chemists. This intermediate allows for the creation of a wide range of complex molecules with diverse applications, including pharmaceuticals, agrochemicals, and other specialty chemicals.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 4, 1990The Journal of Organic Chemistry, 51, p. 2977, 1986 DOI: 10.1021/jo00365a024

InChI:InChI=1/C5H7NO3/c1-4(7)6-2-3-9-5(6)8/h2-3H2,1H3

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 142-26-7 2-acetylaminoethanol 
• 201230-82-2 carbon monoxide 
• 817-87-8 ethyl azidocarbonate 
• 109853-51-2 N-tributylstannyl-2-oxazolidinone 
• 1943-83-5 2-chloroethyl isothiocyanate 
• 598-99-2 Methyl trichloroacetate 
• 64-19-7 acetic acid 
• 443-48-1 metronidazole 
• 611-73-4 Benzoylformic acid 
• 660866-29-5 3-ethynyl-1,3-oxazolidin-2-one 

Downstream Products

• 120224-27-3 3-Acetyl-4-methoxy-oxazolidin-2-one 
• 120224-25-1 4-acetoxy-3-acetyl-1,3-oxazolidin-2-one 
• 141-97-9 ethyl acetoacetate 
• 588-46-5 N-(phenylmethyl)acetamide 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 111873-63-3 3-[2-(4-Hydroxy-phenyl)-acetyl]-oxazolidin-2-one 
• 5396-89-4 benzyl acetoacetate 
• 1120-64-5 2-methyl-4,5-dihydro-1,3-oxazole 
• 60759-49-1 N-acetyl-1,3-oxazol-2-one 
• 497-25-6 dimethylenecyclourethane 
• 463-51-4 Ketene 
• 27584-70-9 4-oxazolin-2-one 
• 1101859-61-3 (S)-N-tert-butyl-5-methyl-4-oxo-6-phenylhexanamide 
• 1101859-64-6 (R)-N-tert-butyl-5-methyl-4-oxo-6-phenylhexanamide 

Relevant academic research and scientific papers

A dichlorination-reductive-dechlorination route to N-acetyl-2-oxazolone

We have shown that sulfuryl chloride is an efficient reagent for the conversion of 2-oxazolidinone into the dichloro derivative, N-acetyl-4,5- dichloro-2-oxazolidinone. Subsequent Zn/AcOH reductive dehalogenation of this trans-dichloride gives N-acetyl-2-oxazolone. The dichloride was previously reported as an undesired side product in the preparation of N-acetyl-2-oxazolone from the monochloro oxazolidinone. In our hands, the dichloride is a key intermediate in a new synthesis of 2-oxazolone, that avoids the use of chlorine gas. Georg Thieme Verlag Stuttgart.

A convenient antibiotic indicator in the ozone treatment of wastewaters. An experimental and theoretical study

N-Acetyl-oxazolidin-2-one has been found to be a convenient indicator in the removal of nitroimidazole-type antibiotic contaminants in wastewaters by ozone since it is the unique product generated in the treatment of waters containing metronidazole, and it is stable against further ozonation in the experimental conditions used. The oxidative conditions imposed by the reaction do not allow isolation of any by-products, nor other stable subproducts. High-performance liquid chromatography coupled with electrospray ionization-time-of-flight mass spectrometry (HPLC-ESI-TOF(MS)) revealed the presence of simple derivatives of both metronidazole and N-acetyl-oxazolidin-2- one, thus indicating that both products are unambiguously connected and that, possibly, a unique reaction pathway would take place in this case. A feasible mechanism for this transformation has then been postulated, which is supported by several experimental findings such as TOC analysis and nitrate titration, both correlating well with the proposed transformation. Furthermore, this mechanism has been evaluated by DFT/B3LYP calculations, showing that the observed product is readily obtained thanks to the high exothermicity displayed by the metronidazole ozonation process.

One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents

A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.

An eco-friendly and highly efficient route for N-acylation under catalyst-free conditions

An eco-friendly, simple, mild, chemoselective and highly efficient procedure for the acylation of primary and secondary amine function in various structurally and electronically aliphatic and aromatic compounds affording their corresponding N-Ac derivatives is developed. Mild conditions, simplicity and easier work-up are the main advantages of this method.

Enantioselective multicomponent synthesis of fused 6-5 bicyclic 2-butenolides by a cascade heterobicyclisation process

The successive coupling of an alkoxy(aryl/heteroaryl)carbene complex of chromium with either a ketone or an imide lithium enolate and then a 3-substituted (H, TMS, PhCH2, PhCH2CH2, Me) propargylic organomagnesium reagent h

Synthesis of N-Acyl carbamates and oxazolidinones using HClO 4-SiO2 as catalyst under solvent-free conditions

Silica supported perchloric acid catalyzes efficiently the reaction of carbamates and oxazolidinones with anhydrides in the presence of silica sulfuric acid under solvent-free conditions. All the reactions were done at room temperature and the N-acyl carb

Short communication: Silica sulfuric acid: A versatile and reusable heterogeneous catalyst for the synthesis of N-ACYL carbamates and oxazolidinones under solvent-free conditions

Silica sulfuric acid catalyzes efficiently the reaction of carbamates and oxazolidinones with anhydrides under solvent-free conditions. All the reactions were done at room temperature and the N-acyl carbamates and oxazolidinones were obtained with high yi

2-Dienylphenacyloxazolones and an intramolecular Diels-Alder approach to the A-B-C ring system of phenanthridone alkaloids

A general route to the A-B-C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels-Alder reaction and hydrolysis.

DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones

Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.

N-Acylation of amides with acid anhydrides by way of dual activation using MgBr2·OEt2

A new practical method for the N-acylation of amides is described. Acylation of various amides with acid anhydrides in the presence of MgBr2·OEt2 gave the corresponding N-acylamides in good to moderate yields. The present method is a