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. 2024 Nov 28;146(49):33675–33711. doi: 10.1021/jacs.4c11556

Scheme 5. Synthesis of Heterotetravalent PROTAC AB3124 (86).

Scheme 5

Reaction conditions: (a) (i) NaH, DMF, 0 °C, 15 min, (ii) allyl bromide, r.t., 16 h; (b) (i) NaH, DMF, r.t., 30 min, (ii) 7, DMF, 60 °C, 16 h; (c) (i) NaH, DMF, r.t., 30 min, (ii) 40, DMF, 60 °C, 16 h; (d) OsO4, NaIO4, 2,6-lutidine, dioxane, H2O, r.t., 16 h; (e) 2-methyl-2-butene, NaH2PO4, NaClO2, t-BuOH, H2O, r.t., 16 h; (f) 14, HATU, DIPEA, DMF, r.t., 2 h; (g) (i) H2, 10% Pd/C, MeOH, r.t., 16 h, (ii) 65, DIPEA, DMSO, 90 °C, 16 h; (h) (i) 4 N HCl in dioxane, MeOH, r.t., 3 h, (ii) 22*, DIPEA, DCM, r.t., 16 h.