2,2-Dimethoxypropane → 3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-2,2-dimethyl-1,3-oxazolidin-4-one

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Reaction Conditions

Reaction Steps

N-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamide (0.35 g, 1.12 mmol), prepared in the previous step, was suspended in 10 mL of toluene, dimethoxypropane (2.0 mL, 16.7 mmol) was added, which was followed by a catalytic amount of p-toluenesulfonic acid monohydrate (20 mg). The mixture was heated to 90° C. for 16 h, then cooled and concentrated under reduced pressure. Flash chromatography (5% acetone/hexane) provided the title compound (210 mg, 53%) as a white solid. HRMS: calcd for C14H13BrN2O2S+H+, 352.99538; found (ESI, [M+H]+), 352.9957. Analytical HPLC: retention time 11.1 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Provenance & Evidence