Pyridine → HCID 67508320, compound

Participants

Reaction Steps

A solution of benzyl 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-ylcarbamate (451 mg, 1.08 mmol) in dichloromethane (5 ml) was cooled to 0° C. Pyridine (200 μl, 2.48 mmol), then acetic anhydride (150 μl, 1.59 mmol) were added. The solution was stirred for 3 hours, and another portion of pyridine (200 μl, 2.48 mmol) then acetic anhydride (150 μl, 1.59 mmol) were added. The solution was stirred for an additional 20 hours, concentrated in vacuo, and the residue purified by flash chromatography (20% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (440.2 mg, 0.959 mmol, 89%). 1H NMR (CDCl3, 400 MHz) δ 1.31 (s, 6H), 2.04 (s, 3H), 2.15-2.20 (m, 2H), 3.09-3.16 (m, 4H), 3.54-3.61 (m, 6H), 3.85 (t, J=5.6 Hz, 2H), 4.16 (m, 2H), 5.02 (s, 3H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 460 [M+H]+, 482 [M+Na]+.

Provenance & Evidence