Reaction of tryptophan with trifluoroacetic anhydride

✍ Scribed by Jan Bergman; Göran Lidgren

• Book ID: 104233196
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 226 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80754-1

✦ Synopsis

Trifluoroacetic anhydride {TFAA) in ether quickly (= 5-10 min) converted tryptophau to the crystalline 2-trifluoromethyl-5(4@-oxazolone (2) without racemization. Dissolution of optically active 2 in acetonitrile gave racemic 2, whereas treatment with hot aqueous dioxane gave the isomeric oxazolone (3). Both 2 and 3, could on heating be further isomer&d to the conjugated oxazolone (4). These oxazolones are interesting starting materials for the preparation of tryptophan containing peptides.