Tert-Butyl nitrite → HCID 58531353, compound

Participants

Reaction Steps

To an ice cold mixture of N-((4′-aminobiphenyl-3-yl)methyl)-3,5-dichloro-N-(4-fluoro-benzyl)-2-hydroxybenzenesulfonamide (0.08 g, 0.15 mmol) in anhydrous acetonitrile (1 mL) and anhydrous THF (1 mL) was added tert-butyl nitrite (0.03 mL, 0.22 mmol) followed by the dropwise addition of azidotrimethylsilane (0.02 mL, 0.17 mmol). The ice bath was removed and the reaction stirred at room temperature. After 1 h, anhydrous THF (0.5 mL) and anhydrous acetonitrile (0.5 mL) were added. After an additional 16 h, the reaction mixture was cooled to 0° C. before tert-butyl nitrite (0.06 mL, 0.44 mmol) and azidotrimethylsilane (0.07 mL, 0.52 mmol) were added. Two hours later, the reaction was quenched with water and extracted twice with chloroform. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 then passed through a RediSep normal phase silica flash column (4 g) eluting with hexane, followed by CHCl3. The appropriate fractions were concentrated in vacuo to afford the title compound (0.04 g, 50%) as a brown glass. 1H NMR (DMSO-d6) δ 7.80-7.75 (m, 1H), 7.57 (d, J=2.5 Hz, 1H), 7.56-7.45 (m, 3H), 7.32 (t, J=7.7 Hz, 1H), 7.28-7.18 (m, 5H), 7.15-7.03 (m, 3H), 4.51 (s, 2H), 4.49 (s, 2H). MS (ESI): 555.3 (M−H)−.

Provenance & Evidence