A nonnutritive sweetener, 6-chloro-d-tryptophan (4), was synthesized from d-tryptophan (1) by nitration, hydrogenation and diazotization, followed by a reaction with cuprous chloride. The optical rotation of 4 agreed with that of an authentic sample which had been prepared by the resolution of racemic 4 methanesulfonate.
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Moriya et al. (1975) studied this question.