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. 2022 Nov 10;12(23):14507–14516. doi: 10.1021/acscatal.2c04511

Scheme 5. (Top) Derivatization of Substrate 3e; (Bottom) X-ray Crystallographic Analysis of 5k and Preparation of a Fluorinated Analogue of the API, UPF-648.

Scheme 5

Reaction conditions: (a) TMS-acetylene (1.5 equiv), Pd(PPh3)2Cl2 (10 mol %), CuI (20 mol %), iPr2NH, 80 °C, 3 h; (b) LiAlH4 (2.2 equiv), THF, 0 °C, 1 h; (c) PhB(OH)2 (1.5 equiv), Pd(PPh3)4 (5 mol %), Cs2CO3 (2.0 equiv), H2O, 1,4-dioxane, 80 °C, 3 h; (d) NaOH (6.0 equiv), MeOH, rt, 5 h; (e) H-Ala-OMe·HCl (1.1 equiv), EDC (1.1 equiv), DMAP (5 mol %), DCM, rt, 16 h. Yields and dr values refer to isolated products.