Potassium Carbonate → HCID 45605619, compound

Participants

Reaction Steps

In analogy to the literature (Moloney et al., J. Med. Chem. 1997, 40, 2347-2362), methyl 3-bromomethylbenzoate (4.75 g, 20.7 mmol) was added to a suspension of hydantoin 1 (5.0 g, 18.6 mmol) and potassium carbonate (3.1 g, 22.5 mmol) in DMF (75 mL) at 23° C. After 18 h, the reaction mixture was partitioned between water and EtOAc, and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water (1×), NaHCO3 (1×), water (1×), brine (1×), then dried over MgSO4. After filtration, concentration in vacuo gave an oil, which was subjected to silica gel chromatography (20→50% EtOAc/hexanes) to yield the desired material as a white sticky foam (8.32 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.92 (m, 2H), 7.58 (m, 1H), 7.34-7.46 (m, 4H), 7.20 (m, 2H), 4.66 (s, 2H), 3.84 (s, 3H), 1.76 (s, 3H).

Provenance & Evidence