492435-15-1

Basic information

• Product Name: (S)-O-benzoyl-N-benzylmandelamide
• Synonyms: (S)-O-benzoyl-N-benzylmandelamide
• CAS NO: 492435-15-1
• Molecular Weight: 345.398
• Mol File: 492435-15-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-O-benzoyl-N-benzylmandelamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-O-benzoyl-N-benzylmandelamide(492435-15-1)
• EPA Substance Registry System: (S)-O-benzoyl-N-benzylmandelamide(492435-15-1)

Safety Data

• Hazardous Substances Data: 492435-15-1(Hazardous Substances Data)

Upstream product

• 82270-62-0 (S)-N-benzylmandelamide 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 100-46-9 benzylamine 
• 17199-29-0 (S)-Mandelic acid 

Relevant articles and documents

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones

Treatment of (-)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1,3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones from chiral O-acylmandelamides or lactamides

(-)-O-Acyllactamides or mandelamides in the presence of TBSOTf underwent cyclization reaction to give optically active 2-oxy-1,3-oxazolidin-4-ones, a novel nitrogen analog of orthoesters, in good yields. An X-ray analysis and NOE studies indicated that the absolute configuration at the newly formed chiral carbon was S. For their synthetic application, the 1,3-dipolar cycloaddition of nitrile oxide was examined. The cycloadducts were obtained in a stereoselective manner. Subsequent treatment of the adduct with TBAF resulted in the one-step removal of mandelamide, giving optically active 4,5-dihydroisoxazole and mandelamide in good yields.