16404-94-7

Basic information

• Product Name: (S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID
• Synonyms: (S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID;(S)-4-Oxoazetidine-2-carboxylic acid;(2S)-4-oxoazetidine-2-carboxylic acid;(S)-(-)-4-Oxo-2-azetidinecarboxylic acid 98%;2-Azetidinecarboxylicacid, 4-oxo-, (2S)-
• CAS NO: 16404-94-7
• Molecular Formula: C₄H₅NO₃
• Molecular Weight: 115.09
• Product Categories: Chiral Building Blocks;Lactams;Organic Building Blocks
• Mol File: 16404-94-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 99-102 °C(lit.)
• Boiling Point: 489.4 °C at 760 mmHg
• Flash Point: 249.8 °C
• Appearance: /
• Density: 1.519 g/cm³
• Vapor Pressure: 6.44E-11mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: 2-8°C
• PKA: 3.19±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID(16404-94-7)
• EPA Substance Registry System: (S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID(16404-94-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 16404-94-7(Hazardous Substances Data)

Usage

Uses

(S)-4-Oxoazetidine-2-carboxylic Acid, is a building block used for various chemical synthesis such as for the synthesis of NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors.

General Description

The crystals of (S)-(-)-4-oxo-2-azetidinecarboxylic acid are orthorhombic and belongs to P212121 space group.

InChI:InChI=1/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)/t2-/m0/s1

Upstream product

• 2791-79-9 dibenzyl L-aspartate 
• 100188-44-1 methyl (S)-(-)-2-oxoazetidine-4-carboxylate 
• 72776-05-7 (S)-benzyl 4-oxoazetidine-2-carboxylate 

Downstream Products

• 28562-53-0 4-acetoxy azetidinone 
• 1558079-05-2 (S)-N-allyl-N-(benzyloxy)-4-oxoazetidine-2-carboxamide 
• 1428535-72-1 thioacetic acid S-{(S)-6-[((S)-4-oxo-azetidine-2-carbonyl)-amino]-6-phenylcarbamoyl-hexyl} ester 
• 1313991-43-3 (3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxo-N-(3-((S)-4-oxoazetidine-2-carboxamido)benzyl)decahydropyrrolo[1,2-a]azocine-3-carboxamide 
• 1258443-85-4 (S)-1-(4-chlorophenyl)-4-oxoazetidine-2-carboxylic acid 
• 95729-65-0 azetirelin 
• 1032188-84-3 (S)-4-oxo-N-(3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propyl)azetidine-2-carboxamide 
• 100188-44-1 methyl (S)-(-)-2-oxoazetidine-4-carboxylate 

Relevant articles and documents

Structures of (S)-(-)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data

The crystal structures of the four-membered heterocycles (S)-(-)-4-oxo-2-azetidinecarboxylic acid (I) and 3-azetidinecar-boxylic acid (II) were solved by direct methods using powder synchrotron X-ray diffraction data. The asymmetry of the oxoazetidine and azetidine rings is discussed, along with the hydrogen bonding.

Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

A NEW SYNTHESIS OF OPTICALLY ACTIVE 2-METHOXYCARBONYL-4-AZETIDINONE FROM L-AZETIDINE-2-CARBOXYLIC ACID: UTILITY OF RUTHENIUM TETROXIDE OXIDATION

A first transformation of L-azetidine-2-carboxylic acid (1) into optically active monocyclic N-unsubstituted β-lactam, (2S)-2-methoxycarbonyl-4-azetidinone (6), has been developed via ruthenium tetroxide (RuO4) oxidation process.