98019-65-9

Usage

Uses

Used in Pharmaceutical Synthesis:
4-OXOAZETIDINE-2-CARBOXYLIC ACID is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new medicinal compounds. Its unique structure and reactivity allow for the creation of diverse drug molecules with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 4-OXOAZETIDINE-2-CARBOXYLIC ACID is utilized as a building block in the production of various agrochemicals. Its incorporation aids in the development of compounds designed to protect crops and enhance agricultural productivity.
Used in Chemical Compound Production:
4-OXOAZETIDINE-2-CARBOXYLIC ACID is used as a fundamental component in the creation of a wide array of chemical compounds. Its versatility in chemical reactions and its capacity to form stable derivatives make it an invaluable asset in the synthesis of specialty chemicals for various applications.
Used in Drug Development:
Due to its potential pharmacological properties, 4-OXOAZETIDINE-2-CARBOXYLIC ACID is employed as a chiral building block in drug development. Its stereochemistry plays a crucial role in the design of enantioselective syntheses, leading to the production of more effective and safer medications.

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 academic research and scientific papers

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.