249734-39-2

Basic information

• Product Name: 2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-
• CAS NO: 249734-39-2
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.283
• Mol File: 249734-39-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-(249734-39-2)
• EPA Substance Registry System: 2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-(249734-39-2)

Safety Data

• Hazardous Substances Data: 249734-39-2(Hazardous Substances Data)

Usage

Chemical compound

2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-

Structure

Complex

Derivative

Methyl ester of 2-azetidinecarboxylic acid

2-Azetidinecarboxylic acid

Cyclic amino acid

Chiral compound

Presence of 1-phenylethyl group

Stereochemistry

(2S)configuration at second carbon atom

Potential applications

Pharmaceutical or biochemical

Research needed

To fully understand properties and potential uses

Upstream product

• 29547-04-4 methyl 2,4-dibromobutanoate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 924630-61-5 2-chloro-4-[methoxycarbonyl-(1-phenyl-ethyl)-amino]-butyric acid methyl ester 
• 1206636-14-7 diphenyl-((2S)-1-((1R)-1-phenylethyl)azetidin-2-yl)-methanol 
• 924630-59-1 1-[1-(1-phenyl-ethyl)-azetidin-2-yl]-propan-1-one 
• 924630-57-9 1-(1-phenyl-ethyl)-azetidine-2-carboxylic acid methoxy-methyl-amide 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: Synthetic and mechanistic aspects

The scope and limitations of a novel intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams from azetidines in high regio- and stereoselectivity is reported. The key step of the process is a SN2-type ring-opening of TMSOTf-activated azetidine rings by silyl ketene acetals generated by treatment with TMSOTf and TEA. This study is a very rare example of nucleophilic ring-opening of azetidines that does not require formation of quaternary azetidinium salts by N-alkylation or the use of N-electron-withdrawing groups. Application of this process to 2-azetidinone system led to a complete change in reactivity and provide 6-aza-bicyclo[3.2.0]heptane derivatives via an unprecedented Mukaiyama aldol-like reaction involving an ester acceptor and a silyl imidate.

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.