Abstract
Trifluoroacetic anhydride (TFAA) in ether quickly (≈ 5–10 min) converted tryptophan to the crystalline 2-trifluoromethyl-5(4H)-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 isomerized to the conjugated oxazolone (4). These oxazolones are interesting starting materials for the preparation of tryptophan containing peptides.
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