Cesium carbonate → HCID 67509085, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (6.70 g, 26.4 mmol) in N,N-dimethylformamide (100 ml) was added 2-(2-(2-chloroethoxy)ethoxy)ethanol (4.0 ml, 28 mmol) and cesium carbonate (8.06 g, 24.7 mmol). The suspension was heated to 70° C. for 17 hours, cooled to room temperature, and concentrated in vacuo. The residue was purified by flash chromatography (20% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (3.32 g, 8.61 mmol, 33%). 1H NMR (CDCl3, 400 MHz) δ 1.31 (s, 6H), 1.95-1.99 (m, 2H), 2.51-2.56 (m, 3H), 2.71 (t, J=5.6 Hz, 2H), 3.55-3.79 (m, 10H), 4.85 (s, 1H), 5.05 (s, 2H), 7.2-7.4 (m, 5H); LRMS (ESI/APCI) m/z 386 [M+H]+, 408 [M+Na]+.

Provenance & Evidence