Tetrahedron Letters p. 4597 - 4600 (1989)
Update date:2022-08-31
Topics:
Bergman, Jan
Lidgren, Goeran
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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(1983)Doi:10.1021/ja00034a052
(1992)Doi:10.1039/c4cc02175d
(2014)Doi:10.1039/c9tc06702g
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