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Weinstein, Adam B.; Bachrach, Florence J.; Cagulada, Amy; Regens, Christopher S.; Zhang, Peng
Organic process research & development, 11/2023, Letnik: 27, Številka: 11Journal Article
The chiral amino alcohol (R)-2-amino-2-methylhexan-1-ol (1) is a key fragment in the synthesis of selgantolimod, a TLR8 agonist that is being evaluated for the treatment of hepatitis B infection. This report describes the development of a robust and scalable synthesis of the targeted amino alcohol featuring a hydrolase-catalyzed kinetic resolution of an α,α-disubstituted amino ester. The results highlight considerations for substrate design for the enzymatic resolution, the impact of pH on the resolution of an unprotected α,α-disubstituted amino ester derivative, and implementation of this substrate within a route to the desired amino alcohol fragment.
