39897-13-7

Usage

Uses

Used in Pharmaceutical Research:
(S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid is used as a starting material for the synthesis of various drugs and biologically active molecules. Its unique structure and functional groups enable the development of new compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid is used as a building block for creating complex molecular structures. The sulfonyl group enhances the reactivity of the molecule, allowing for a wide range of chemical reactions and the formation of diverse molecular scaffolds.
Used in Academic Chemistry:
(S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid is utilized in academic research to explore its potential applications and to study the effects of its unique structure on chemical reactions and molecular interactions.
Used in Industrial Chemistry:
In the industrial chemistry sector, (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid is employed as a key intermediate in the production of various pharmaceuticals and other chemical products. Its versatility and stability make it a valuable component in the synthesis of a wide range of compounds.

Upstream product

• 1022820-87-6 p-toluenesulfonylaminomalonic acid diethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 2517-04-6 Azetidine-2-carboxylic acid 
• 352018-64-5 (R)-4-N-(p-toluenesulfonyl)amino-2-chlorobutyric acid 
• 1414846-32-4 (S)-1-((S)-1-tosylazetidin-2-yl) ethane-1,2-diol 
• 1414846-31-3 (S)-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)-1-tosylazetidine 
• 10396-97-1 4-methyl-N-((S)-2-oxotetrahydrofuran-3-yl)benzenesulfonamide 
• 960004-46-0 (S)-methyl 1-tosylazetidine-2-carboxylate 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 
• 10019-95-1 N-tosylpyrrolidinone 
• 178946-64-0 3-bromo-1-tosylpyrrolidin-2-one 
• 116283-38-6 2-[2-(Toluene-4-sulfonylamino)-ethyl]-malonic acid dimethyl ester 
• 116241-31-7 1-(Toluene-4-sulfonyl)-azetidine-2,2-dicarboxylic acid dimethyl ester 
• 116241-36-2 1-(Toluene-4-sulfonyl)-azetidine-2,2-dicarboxylic acid 

Downstream Products

• 17330-26-6 (1-tosylazetidin-2-yl)methanol 
• 868272-74-6 2-Diazo-1-[(S)-1-(toluene-4-sulfonyl)-azetidin-2-yl]-ethanone 
• 960004-46-0 (S)-methyl 1-tosylazetidine-2-carboxylate 
• 554434-23-0 (S)-1-(Toluene-4-sulfonyl)-azetidine-2-carboxylic acid ((S)-1-hydroxymethyl-2-phenyl-ethyl)-amide 
• 2517-04-6 Azetidine-2-carboxylic acid 

Relevant academic research and scientific papers

Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems

Cyclic enamines are important synthons for many synthetic and pharmacological targets. Here, we report an inexpensive, catalyst-free, multigram-scale synthesis for cyclic enamines with exocyclic double bonds and four- to seven-membered rings. This strategy is more conducive to scale up, permissive of functionalization around the cyclic system, and less sensitive to the nature of the N-protecting group than previously-described methods for cyclic enamine synthesis. Further, we explore application of these enamines to the synthesis of highly-strained spirocyclic 3N-cyclopropyl scaffolds.

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

An efficient synthesis of azetidines with (2-bromoethyl)sulfonium triflate

Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesi

Enantiodivergent synthesis of N-protected azetidine-2-carboxylic acid

A new route to both enantiomers of N-tosyl-azetidine-2- carboxylic acid has been developed from (R)-2-cyclohexylideneglyceraldehyde which proceeded with good overall yield and excellent enantiomeric purity.

Thermal Arndt-Eistert reactions of N-tosyl cyclic α-amino acids

Thermal Arndt-Eistert reactions of N-tosyl cyclic α-amino acids were studied to explore the preparation of α,β-unsaturated esters bearing a terminal tosylamino group. For L-N-tosyl-aziridine 2-carboxylic acid and L-N-tosyl-azetidine 2-carboxylic acid, the corresponding (E)-α,β- unsaturated esters were obtained stereospecifically. Copyright Taylor & Francis, Inc.

Process for preparation of optically active n-substituted azetidine-2-carboxylic acids

The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-sub

Peptidyl aldehyde inhibitors of calpain incorporating P2-proline mimetics

Four new peptidyl aldehydes bearing proline mimetics at the P2-position were synthesized and studied as inhibitors of calpain I, cathepsin B, and selected serine proteases. The ring size of the P2-constraining residue influenced the

PROCESS FOR PREPARATION OF OPTICALLY ACTIVE N-SUBSTITUTED AZETIDINE-2-CARBOXYLIC ACIDS

The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-sub

Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate

Three new chiral dirhodium(II) tetracarboxylate catalysts, based on azetidine- and aziridine-2-carboxylic acid, were prepared. Their selectivities in the cyclopropanation reaction of methyl phenyl-diazoacetate and olefins were determined in solvents of de

A New Anodic C-N Bond Forming Reaction Useful to Formation of Aziridine, Azetidine, and Pyrrolidine Rings

Aziridine, azetidine, and pyrrolidine rings were formed in high yields by oxidation of the corresponding dimethyl α-(ω-tosylaminoalkyl)malonates in methanol containing KI as a mediator.