Cesium carbonate → Benzyl 14-methyl-2,5,8-trioxa-11-thiapentadecan-14-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (2.05 g, 8.1 mmol) in N,N-dimethylformamide (10 ml) was added cesium carbonate (2.27 g, 6.97 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (2.32 g, 7.29 mmol). The solution was heated to 60° C. for 2 hour, then 70° C. for 16 hour, cooled to room temperature, concentrated in vacuo, and the residue dissolved in 50 ml 5% NaHSO4, extracted with 3×50 ml ethyl acetate, dried on MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (10% to 60% ethyl acetate in hexanes) to give the title compound as a clear oil (1.24 g, 3.10 mmol, 60%). 1H NMR (400 MHz, CDCl3) δ 1.32 (s, 6H), 1.99 (m, 2H), 2.53 (m, 2H), 2.73 (m, 2H), 3.39 (s, 3H), 3.5-3.7 (m, 10H), 4.8 (s, 1H), 5.05 (s, 2H), 7.3-7.4 (m, 5H). LRMS (ESI/APCI) m/z 422 [M+Na]+.

Provenance & Evidence