361459-12-3

Basic information

• Product Name: Propanoic acid, 3-[(1-methylethyl)[(1S)-1-phenylethyl]amino]-3-oxo-
• CAS NO: 361459-12-3
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Mol File: 361459-12-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 3-[(1-methylethyl)[(1S)-1-phenylethyl]amino]-3-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 3-[(1-methylethyl)[(1S)-1-phenylethyl]amino]-3-oxo-(361459-12-3)
• EPA Substance Registry System: Propanoic acid, 3-[(1-methylethyl)[(1S)-1-phenylethyl]amino]-3-oxo-(361459-12-3)

Safety Data

• Hazardous Substances Data: 361459-12-3(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 75815-80-4 (1S)-N-(1-methylethylidene)-1-phenylethylamine 
• 19302-32-0 (S)-N-isopropyl-1-phenylethylamine 
• 361459-11-2 ethyl 1-[N-(1(S)-phenylethyl)-N-isopropylamino]carbonylacetate 

Relevant articles and documents

Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'

The general purpose of this work is to investigate the potential of biomimetic NAD+ models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD+ analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlaender approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%).