106745-99-7

Upstream product

• 106942-43-2 4-Benzyl-4-(2,2-difluoro-acetyl)-2-phenyl-4H-oxazol-5-one 
• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 98-88-4 benzoyl chloride 
• 2566-22-5 DL-N-benzoylphenylalanine 
• 150-30-1 Phenylalanine 

Relevant academic research and scientific papers

Peptidase inhibitors

This invention relates to analogs of peptidase substrates in which the amide group containing the scissile amide bond of the substrate peptide has been replaced by an activated electrophilic ketone moiety. These analogs of the peptidase substrates provide specific enzyme inhibitors for a variety of proteases, the inhibition of which will have useful physiological consequences in a variety of disease states.

Synthesis of Fluorinated α-Amino Ketones, III. Preparation of Fluorinated Ketone Analogues of Phenylalanine, Lysine, and p-(Guanidino)phenylalanine

The synthesis of α-amino mono-, di-, and trifluoromethyl and difluoromethylene ketones and their derivatives is described.A one-pot sequence related to the Dakin-West reaction starts from amino acids and gives the corresponding fluorinated ketone analogue

SYNTHESIS OF FLUORINATED α-AMINO KETONES PART I: α-BENZAMIDOALKYL MONO- DI- AND TRIFLUOROMETHYL KETONES

2-Phenyl-5(4H)-oxazolones, obtained from α-amino acids, are reacted with di- and trifluoro acetic anhydride by a modified Dakin-West procedure to yield in a one-pot reaction α-benzamidoalkyl-di- and trifluoromethyl ketones in good yields.The monofluoromethyl analogues were also prepared from α-amino acids, however the use of the highly toxic fluoroacetic anhydride was avoided.The key step is the halogen exchange reaction on the corresponding bromomethyl ketone.