216578-90-4

Basic information

• Product Name: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide
• Synonyms: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide
• CAS NO: 216578-90-4
• Molecular Weight: 266.272
• Mol File: 216578-90-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide(216578-90-4)
• EPA Substance Registry System: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide(216578-90-4)

Safety Data

• Hazardous Substances Data: 216578-90-4(Hazardous Substances Data)

Upstream product

• 216578-88-0 (RS)-N-benzyl-2-(2,5-dioxo-1-pyrrolidinyl)-2-fluoroethanamide 
• 100-46-9 benzylamine 
• 216578-83-5 (RS)-N-benzyl-2-chloro-2-fluoroethanamide 
• 216578-85-7 (RS)-N-benzyl-2-fluoro-2-iodoethanamide 

Downstream Products

• 1130888-15-1 C₁₅H₁₈N₂O₂S₂ 

Relevant articles and documents

Synthesis and reactions of α-fluoro-α-amino amides

N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected α-fluoro-α-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The α-fluoro-α-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding α-fluorobetaine amide, and subsequent acidic hydrolysis led to α-fluorobetaine as the first example of an 'unprotected' α-fluoroamino acid.