4-Acetoxy-2-azetidinone

Base Information

• Chemical Name: 4-Acetoxy-2-azetidinone
• CAS No.: 28562-53-0
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 2933790090
• European Community (EC) Number: 249-083-7
• DSSTox Substance ID: DTXSID20951247
• Nikkaji Number: J250.737D
• Wikidata: Q17122082
• ChEMBL ID: CHEMBL122408
• Mol file: 28562-53-0.mol

Synonyms:4-acetoxy-2-azetidinone

Chemical Property of 4-Acetoxy-2-azetidinone

Chemical Property:

• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: 38-40 °C(lit.)
• Refractive Index: 1.476
• Boiling Point: 296.45 °C at 760 mmHg
• PKA: 13.41±0.40(Predicted)
• Flash Point: 133.089 °C
• PSA: 55.40000
• Density: 1.269 g/cm³
• LogP: -0.27570
• Storage Temp.: 2-8°C
• Solubility.: formic acid: soluble50mg/mL, clear, yellow-orange
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

97% ^*data from raw suppliers

4-Acetoxy-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(=O)N1
• General Description: 4-Acetoxy-2-azetidinone serves as a key intermediate in the synthesis of penem antibiotics, where it is converted into metal mercaptides (e.g., silver or mercury) and subsequently acylated and cyclized to form 2-substituted penem-3-carboxylates. Its utility lies in enabling the introduction of diverse substituents at the penem nucleus's 2-position, facilitated by tritylthio groups, while maintaining stability as an intermediate for further functionalization. 4-Acetoxy-2-azetidinone plays a crucial role in expanding the structural diversity of β-lactam antibiotics.

Technology Process of 4-Acetoxy-2-azetidinone

There total 16 articles about 4-Acetoxy-2-azetidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-azetidinone (930-21-2) + peracetic acid (79-21-0) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With Ru-carbon; sodium acetate; acetic acid; In ethyl acetate; for 2.5h; Ambient temperature;

DOI:10.1021/ja00177a067

Reference yield: 89.0%

4-Trimethylsilylazetidin-2-one (80395-83-1) + acetic acid (64-19-7,77671-22-8) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With tetraethylammonium tosylate; In acetonitrile; Ambient temperature; constant current electrolysis;

Reference yield: 88.0%

2-azetidinone (930-21-2) + acetic acid (64-19-7,77671-22-8) → 4-acetoxy azetidinone (28562-53-0)

Guidance literature:

With oxygen; sodium acetate; acetaldehyde; ruthenium trichloride; In ethyl acetate; at 40 ℃;

DOI:10.1016/S0040-4039(00)79446-9

upstream raw materials:

2-azetidinone

peracetic acid

acetic acid

vinyl acetate

Downstream raw materials:

Trithiocarbonic acid 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester 4-oxo-azetidin-2-yl ester

di-2-(p-nitrobenzyloxycarbonylamino)ethyl trithiocarbonate

3-(4-Oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl)-propionic acid 4-nitro-benzyl ester

4-(4-Oxo-azetidin-2-yloxy)-benzoic acid

Refernces

Nuclear analogs of β-lactam antibiotics. XIV. Synthesis of penems via (4-tritylthio-2-azetidinon-1-yl)triphgenylphoiphoranylideneacetates

10.1139/v82-142

The research focuses on the synthesis of penems, a class of β-lactam antibiotics, via the preparation of (4-tritylthio-2-azetidinon-1-yl)triphenylphosphoranylideneacetates from 4-acetoxyazetidin-2-one. The process involves converting the starting material into metal mercaptides (silver or mercury), which are then acylated and cyclized to form 2-substituted penem-3-carboxylates. The study highlights the versatility of using trityl groups to allow for the introduction of different substituents at position 2 of the penem nucleus, and the stability of the mercaptides as intermediates, which can be stored and readily acylated to produce a variety of penem analogs.