16404-94-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID is used as a key building block for the synthesis of various pharmaceutical compounds, including NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors. Its unique structure and properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
(S)-(-)-4-OXO-2-AZETIDINECARBOXYLIC ACID is used as a versatile building block for the synthesis of a wide range of chemical compounds. Its ability to form stable bonds and its unique molecular structure make it an essential component in various chemical reactions and processes.

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 
• 95729-65-0 azetirelin 
• 1258443-85-4 (S)-1-(4-chlorophenyl)-4-oxoazetidine-2-carboxylic acid 
• 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 
• 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 academic research and scientific papers

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.

Syntheses of hydroxamic acid-containing bicyclic β-lactams via palladium-catalyzed oxidative amidation of alkenes

Palladium-catalyzed oxidative amidation has been used to synthesize hydroxamic acid-containing bicyclic β-lactam cores. Oxidative cleavage of the pendant alkene provides access to the carboxylic acid in one step.

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.

Carbon based nucleophilic ring opening of activated monocyclic β-lactams; synthesis and stereochemical assignment of the ACE inhibitor WF-10129

The preparation of γ-keto α-amino acids via carbon based nucleophilic ring opening of activated monocyclic β-lactams was examined and applied to the synthesis and stereochemical assignment of the dipeptide angiotensin convering enzyme (ACE) inhibitor, WF-

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.