Potassium Hydroxide → HCID 67508690, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-(2-hydroxy-2-(oxiran-2-yl)ethylthio)-2-methylbutan-2-ylcarbamate (3.33 g, 9.81 mmol) in dimethylsulfoxide (50 ml) and H2O (10 ml) was added 5.0 M KOH (600 μl, 3.0 mmol). The solution was heated to 90° C. for 5 hour, cooled to room temperature, diluted with 400 ml ethyl acetate, washed with 1×200 ml 5% NaHSO4, 5×200 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. The residue was purified by preparatory HPLC (H2O/acetonitrile) to give the title compound as a clear oil (159.3 mg, 0.446 mmol, 45%) as a mixture of diastereomers. 1H NMR (400 MHz, CDCl3) δ 1.28 (s, 6H), 1.9-2.1 (m, 2H), 2.50 (m, 2H), 2.6-2.7 (m, 2H), 3.6-3.8 (m, 4H), 3.85 (br s, 3H), 4.93 (s, 1H), 5.04 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 358 [M+H]+, 380 [M+Na]+.

Provenance & Evidence