Synthesis of Deuterated CycloDOPA with Hydrogen/Deuterium Exchange

Hashimoto, Makoto; Tachrim, Zetryana Puteri; Nakagawa, Souichi; Nakamura, Tadashi; Ohashi, Fumina; Kurokawa, Natsumi; Wakasa, Haruna; Tokoro, Yurika; Sakihama, Yasuko; Hashidoko, Yasuyuki; Suzuki, Takeyuki

doi:10.3987/com-18-s(f)33

Cited by 2 publications

(1 citation statement)

References 17 publications

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“…Deuterated TfOH (TfOD) is already reported as an acid H–D exchange reagent for aromatic compounds. Our group has intensively studied the role of TfOD in aromatic deuteration of optically active α‐amino acids 10 and peptides, 17 indole‐3‐propionic acid derivatives, 18 selective deuteration in cyclodopa derivatives, 19 as well as the imidazole ring deuteration of histidine and histamine 20 . Very recently, the deuteration of meta ‐substituted aniline derivatives, N ‐acetyl benzylamine, paracetamol, and several nitrogen‐containing pharmaceuticals has been reported and involving utilization of TfOD under a range of temperature condition 21 …”

Section: Introductionmentioning

confidence: 99%

Mild and selective hydrogen–deuterium exchange for aromatic hydrogen of amines

Tachrim,

Hashinoki,

Wang

et al. 2023

Labelled Comp Radiopharmac

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The direct electrophilic deuteration of the aromatic moiety in aromatic and aralkyl amines is reported. The acid‐catalyzed deuteration is facilitated by deuterated trifluoromethanesulfonic acid, [D]triflic acid, CF3SO3D, TfOD, which acts as both the reaction solvent and the source of the deuterium label. The mild conditions enable room temperature hydrogen/deuterium exchange for most of the para‐substituted aromatic amine derivatives studied. In addition, short reaction times and a high degree of aromatic deuteration are achieved and isolation of the product is simple. The optical activity of the chiral aralkyl amines studied was preserved.

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