Hydrochloric Acid → HCID 178502286, compound

Participants

Reaction Steps

To a solution of ((S)-1-{(S)-8-[4-(4-Bromo-phenyl)-1H-imidazol-2-yl]-1,4-dioxa-7-aza-spiro[4.4]nonane-7-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (450 mg, 0.89 mmol) in dioxane (8 mL) and water (4 mL) was added 4-boronobenzoic acid (154 mg, 0.93 mmol), sodium carbonate (189 mg, 1.78 mmol), and tetrakis(triphenylphosphine)-palladium(0) (104 mg, 0.09 mmol) and the reaction mixture was stirred at reflux for 3 h under nitrogen. The pH was adjusted to 1 with 2 M HCl, and the reaction mixture was extracted with EtOAc (3×20 mL). The organic layers were combined, dried over sodium sulfate, concentrated and purified by flash chromatography (eluted with methanol in DCM, 0 to 7%) to provide the title intermediate as a yellow solid (330 mg, 68% yield). (m/z): [M+H]+ calcd for C29H32N4O7 549.23. found 549.3. 1H NMR (CH3OD, 400) δ (ppm) 8.13-8.11 (m, 2H), 7.90-7.78 (m, 7H), 5.39-5.34 (m, 1H), 4.19-3.91 (m, 7H), 3.66 (s, 3H), 2.72-2.65 (m, 1H), 2.48-2.41 (m, 1H), 2.12-1.95 (m, 1H), 0.92-0.85 (m, 6H).

Provenance & Evidence