The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: H-Trp-OMe.HCl( cas:7524-52-9 ) is researched.Quality Control of H-Trp-OMe.HCl.Vallakati, Ravikrishna; Plotnikov, Abel T.; Altman, Ryan A. published the article 《Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions》 about this compound( cas:7524-52-9 ) in Tetrahedron. Keywords: deuterated tryptophan synthesis stability; tryptophan borylation deuteration iridium catalyst deprotection scrambling reaction; C–H Borylation; Deborylative deuteration; Deuterium labeling; L-Tryptophan; Metal-Catalysis. Let’s learn more about this compound (cas:7524-52-9).
Herein, we report a practical synthesis of 2-D-L-tryptophan via sequential Ir-catalyzed C-H borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc (Boc = tert-butoxycarbonyl) and Me ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D-L-tryptophan is stable in many buffers used for biol. studies.
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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem