1254975-36-4

Upstream product

• 63-91-2 L-phenylalanine 
• 35016-63-8 (S)-2-bromo-3-phenylpropionic acid 

Downstream Products

• 1415408-84-2 (2S)-2-bromo-3-phenylpropanenitrile 
• 1415408-82-0 (2S)-2-bromo-3-phenylpropanamide 
• 1255738-02-3 C₂₀H₂₂BrN₃O₄S 
• 1255738-02-3 O-2'-bromo-3'-phenylpropanoyl-1-benzenesulfonylpyrrolidine-2-carboxamidoxime 
• 1254975-33-1 (2'S,5R)-5-benzyl-3-(1'-benzenesulfonylpyrrolidin-2'-yl)-4,5-dihydro-1,2,4-oxadiazin-6-one 

Relevant academic research and scientific papers

Synthesis of enantiomerically enriched-bromonitriles from amino acids

Two methods were investigated for the preparation of six chiral-bromonitriles with different optic purities. The nitrous deamination of amino acids gives-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding-bromoamids using thionyl chloride gives-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

Synthesis, antibacterial and antifungal activities of new chiral 5-alkyl-3-(1′-benzenesulfonylpyrrolidin-2′-yl)-4,5-dihydro-1,2, 4-oxadiazin-6-ones

Chiral α-bromoacid chlorides can be easily prepared from amino acids. Their condensation with new 1-benzenesulfonylpyrrolidin-2-carboxamidoxime derived from proline lead to the corresponding O-(bromoacyl) amidoximes. The latter afforded new chiral 5-alkyl-3-(1′-benzenesulfonylpyrrolidin- 2′-yl)-4,5-dihydro-1,2,4oxadiazin-6-ones in good chemical yields via intramolecular cyclization in the presence of one equivalent of NaH. These new compounds were evaluated for their antibacterial and antifungal activities using micro-dilution tests against some strains of bacteria and fungi. Our compounds showed an excellent antibacterial activity, which is better than the drug levofloxacin.