Hydrochloric Acid → HCID 86703615, compound

Participants

Reaction Steps

To a mixture of 4-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-2-fluorobenzamide in tetrahydrofuran (5 mL) was added 1 N hydrochloric acid (10 mL) and the reaction mixture was stirred for 16 hours at ambient temperature. After diluting the mixture with dichloromethane (50 mL), the organic phase was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by reverse-phase preparative HPLC to afford the title compound as a colorless solid (0.073 g, 22%): 1H NMR (300 MHz, DMSO-d6) δ 11.66 (br s, 1H), 7.80-7.70 (m, 1H), 6.97-6.85 (m, 1H), 5.29-5.16 (m, 1H), 5.01-4.90 (m, 1H), 4.15-3.90 (m, 4H), 3.71-3.51 (m, 2H), 3.38-3.29 (m, 2H), 2.23-1.90 (m, 3H), 1.80-1.53 (m, 12H), 1.35-1.23 (m, 3H); MS (ES−) m/z 465.2 (M−1).

Provenance & Evidence