178601-78-0

Basic information

• Product Name: (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide
• Synonyms: (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide
• CAS NO: 178601-78-0
• Molecular Weight: 411.414
• Mol File: 178601-78-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide(178601-78-0)
• EPA Substance Registry System: (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide(178601-78-0)

Safety Data

• Hazardous Substances Data: 178601-78-0(Hazardous Substances Data)

Upstream product

• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 85-44-9 phthalic anhydride 
• 17451-66-0 N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine 
• 175476-28-5 (S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-nitro-phenyl)-propionamide 

Downstream Products

• 129446-45-3 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 

Relevant articles and documents

Neighbouring group effects promote substitution reactions over elimination and provide a stereocontrolled route to chloramphenicol

In reactions of β-brominated valine and p-nitrophenylalanine derivatives to give β-hydroxy amino acid derivatives the carboxyl group, when protected as an amide, exerts a neighbouring group effect to facilitate the substitution process, and reduce competing elimination reactions. As a consequence of the effect, the (2R,3R)- and (2R,3S)-stereoisomers of 3-bromo-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamide both react to give (2S,3R)-3-hydroxy-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamid e, providing a stereoconvergent route to chloramphenicol.