125639-95-4

Basic information

• Product Name: 2-Azetidinone, 4-acetyl-3-ethyl-, trans- (9CI)
• Synonyms: 2-Azetidinone, 4-acetyl-3-ethyl-, trans- (9CI)
• CAS NO: 125639-95-4
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.16774
• Product Categories: ACETYLGROUP
• Mol File: 125639-95-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Azetidinone, 4-acetyl-3-ethyl-, trans- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-acetyl-3-ethyl-, trans- (9CI)(125639-95-4)
• EPA Substance Registry System: 2-Azetidinone, 4-acetyl-3-ethyl-, trans- (9CI)(125639-95-4)

Safety Data

• Hazardous Substances Data: 125639-95-4(Hazardous Substances Data)

Usage

Isomer

trans isomer of 4-acetyl-3-ethyl-2-pyrrolidinone

Uses

manufacturing of pharmaceuticals and organic compounds

Potential

synthesis of novel heterocyclic compounds

Building block

synthesis of biologically active compounds

Starting material

preparation of drugs and pharmaceutical products

Upstream product

• 116078-98-9 (3R,4S)-3-ethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone 
• 116078-97-8 (3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-ethyl>-2-azetidinone 
• 103289-67-4 (3R,4R)-3-ethyl-4-trimethylsilylethynyl-2-azetidinone 

Relevant articles and documents

β-Lactams from Ester Enolates and Silylimines: Enantioselective Synthesis of the trans-Carbapenem Antibiotics (+)-PS-5 and (+)-PS-6

A new synthetic route to the antibiotics (+)-PS-5 and (+)-PS-6 is described.The preparation involves a fully stereocontrolled reaction between the enantiomerically pure N-trimethylsilylimine of lactic or mandelic aldehyde and the lithium enolate of the tert-butyl butanoate or tert-butyl isovalerate, respectively.Conversion of the azetidinones obtained to 4-acetoxy derivatives via oxidative cleavage of the hydroxyethyl or hydroxybenzyl side chain and introduction of the necessary appendage in the position 4 of the azetidinone ring, followed by assemlage of the bicyclic ring system, afforded the natural trans-carbapenems (+)-PS-5 and (+)-PS-6.

Azetidinone derivatives and processes for production thereof

The invention relates to a method of producing an azetidinone derivative of the formula: STR1 which comprises reacting a compound of the formula STR2 with a compound of the formula STR3 and then subjecting the resulting compound to hydrolysis, the substituents above being as defined in the specification.