215593-41-2

Basic information

• Product Name: (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide
• Synonyms: (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide
• CAS NO: 215593-41-2
• Molecular Weight: 263.337
• Mol File: 215593-41-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide(215593-41-2)
• EPA Substance Registry System: (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide(215593-41-2)

Safety Data

• Hazardous Substances Data: 215593-41-2(Hazardous Substances Data)

Upstream product

• 6310-21-0 2-(1,1-dimethylethyl)-benzenamine 
• 36394-75-9 (S)-2-acetoxypropanoyl chloride 
• 535-17-1 (S)-2-acetoxypropionic acid 

Relevant articles and documents

Further study of axial chirality due to an acyclic imide N-Ar bond: Control of rotational barrier by electronic effects of acyl groups

Studies on stability to racemization in a series of optically active N-aroyl-N-(2-t-butylphenyl)acetamides 2a-g (X=NMe2, OMe, Me, H, F, Cl, CF3), depending on the electronic effect of their aroyl groups, are described. It has been revealed that the stability of 2 bearing stronger electron-withdrawing groups on the aroyl benzene ring was enhanced, with linear correlation between the ΔG? and Hammett's σp para-substituent constant of 2a-g. Furthermore, the absolute configuration of optically active imides 2a-g has been determined by comparison with the CD spectrum of (S)-N-(2-t-butylphenyl)-N-(4-trifluoromethylbenzoyl)propionamide (5b) derived from (Ra,2S)-N-(2-t-butylphenyl)-N-(4-trifluoromethylbenzoyl)-2- acetoxypropionamide (4b), whose absolute configuration was determined by X-ray analysis.

SmI2-mediated reduction of α-functionalised amides: Highly enantiospecific access to an atropisomeric amide

SmI2 or SmI2-LiCl mixtures can be used to reduce α-functionalised amides in yields of up to 85% depending upon the amide structure. The method has been applied to the synthesis of an atropisomeric anilide system in highly enantioenriched form, starting with (S)-O-acetyl lactic acid.