Synthesis of α,β-dehydrotryptophan by reaction of indole with the β-(N-methylamino)dehydroalanine derivative

Article abstract of DOI:10.1016/S0040-4039(97)10850-4

α,β-Dehydrotryptophan 4 is synthesized by a sequence of reactions starting with the corresponding serine derivative 1. This procedure includes substitution reaction between indole and the methylamino group of the β-(N-methylamino)dehydroalanine derivative 3 in acetic acid. The key intermediate 3 is obtained by oxidation of 1 with dimethylsulfoxide activated by p-toluenesulfonyl chloride, followed by reaction of the resulting β-O-tosyldehydroserine 2 with methylamine.