98019-65-9

Basic information

• Product Name: 4-OXOAZETIDINE-2-CARBOXYLIC ACID
• Synonyms: 4-OXOAZETIDINE-2-CARBOXYLIC ACID;2-Azetidinecarboxylic acid, 4-oxo-;4-Carboxyazetidin-2-one
• CAS NO: 98019-65-9
• Molecular Formula: C₄H₅NO₃
• Molecular Weight: 115.0874
• Mol File: 98019-65-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 489.4°C at 760 mmHg
• Flash Point: 249.8°C
• Appearance: /
• Density: 1.519g/cm³
• Vapor Pressure: 6.44E-11mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.19±0.20(Predicted)
• CAS DataBase Reference: 4-OXOAZETIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXOAZETIDINE-2-CARBOXYLIC ACID(98019-65-9)
• EPA Substance Registry System: 4-OXOAZETIDINE-2-CARBOXYLIC ACID(98019-65-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 98019-65-9(Hazardous Substances Data)

Usage

General Description

4-OXOAZETIDINE-2-CARBOXYLIC ACID, also known as oxoazetidine carboxylic acid, is an organic compound with the molecular formula C4H5NO3. It is a cyclic four-membered lactam with a carboxylic acid functional group. 4-OXOAZETIDINE-2-CARBOXYLIC ACID is used in the synthesis of pharmaceuticals and agrochemicals. It is also used as a building block in the production of various chemical compounds. It is important in the field of drug development due to its potential pharmacological properties and ability to act as a chiral building block in the synthesis of various drug molecules.

InChI:InChI=1/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)

Synthetic route

benzyl (2R)-4-oxoazetidine-2-carboxylate (95729-87-6) → (2R)-2-azetidinone-4-carboxylic acid (98019-65-9)

Conditions	Yield
In methanol; palladium-carbon

peracetic acid (79-21-0) + (2R)-2-azetidinone-4-carboxylic acid (98019-65-9) → 4-acetoxy azetidinone (28562-53-0)

Conditions	Yield
With Ru-carbon; sodium acetate; acetic acid In ethyl acetate for 2.5h; Ambient temperature;	82%

(2R)-2-azetidinone-4-carboxylic acid (98019-65-9) + sodium acetate (127-09-3) → 4-acetoxy azetidinone (28562-53-0)

Conditions	Yield
In water; acetonitrile Kolbe-type electrolysis, Pt electrodes, undivided cell; other 4-carboxy-2-azetidinones;	76%
In acetic acid; acetonitrile Kolbe-type electrolysis, Pt electrodes, undivided cell;	76%

(2R)-2-azetidinone-4-carboxylic acid (98019-65-9) + acetic acid (64-19-7) → 4-acetoxy azetidinone (28562-53-0)

Conditions	Yield
In acetonitrile electrolysis: platinum electrodes, undivided cell, NaOAc electrolyte;	76%

(2R)-2-azetidinone-4-carboxylic acid (98019-65-9) + isopropyl (2S)-4-[[3-(aminocarbamothioylamino)-5-chloro-2-methylphenyl] methyl]-2-methylpiperazine-1-carboxylate → isopropyl (2S)-4-[[5-chloro-2-methyl-3-[[5-[(2S)-4-oxoazetidin-2-yl]-1,3,4-oxadiazol-2-yl]amino]phenyl]methyl]-2-methylpiperazine-1-carboxylate

Conditions	Yield
With 1-ethyl-3-(3-methylaminopropyl)-carbodiimide hydrochloride In dichloromethane for 2h;	42%

1-(3-bromophenyl)-1H-pyrazole (294877-33-1) + (2R)-2-azetidinone-4-carboxylic acid (98019-65-9) + ammonium acetate (631-61-8) → 4-(3-(1H-pyrazol-1-yl)phenyl)azetidin-2-one acetate

Conditions

Yield

Stage #1: 1-(3-bromophenyl)-1H-pyrazole; (2R)-2-azetidinone-4-carboxylic acid With [nickel(II)(4,4'-di-tert-butyl-2,2'-bipyridine)(chloride)2]; (4,4′-di-t-butyl-2,2′-bipyridine)bis[3,5-difluoro-2-[5-trifluoromethyl-2-pyridinyl-kN]phenyl-kC]iridium(III) hexafluorophosphate; caesium carbonate In N,N-dimethyl acetamide for 48h; Irradiation; Inert atmosphere; Stage #2: ammonium acetate In water; acetonitrile

Upstream product

• 95729-87-6 benzyl (2R)-4-oxoazetidine-2-carboxylate 

Downstream Products

• 28562-53-0 4-acetoxy azetidinone 

Relevant articles and documents

4-Substituted-2-azetidinone compound, process of producing the compounds, and medicaments containing the compounds

A novel 4-substituted-2-azetidinone compound shown by the general formula STR1 and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in schizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.