Cesium carbonate → Benzyl 4-(2-hydroxyethylthio)-2-methylbutan-2-ylcarbamate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (3.30 g, 12.2 mmol) in N,N-dimethylformamide (50 ml) was added iodoethanol (1.4 ml, 18.0 mmol) and cesium carbonate (390 mg, 1.20 mmol). The solution was heated to 85° C. for 16 hours, cooled to room temperature, and concentrated in vacuo. The residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (1.01 g, 3.40 mmol, 26%). 1H NMR (400 MHz, CDCl3) δ 1.31 (s, 6H), 2.0-2.1 (m, 2H), 2.47-2.51 (m, 2H), 2.72 (m, 2H), 3.70 (m, 2H), 4.7 (s, 1H), 5.06 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 298 [M+H]+, 320 [M+Na]+.

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