Sodium hydride → HCID 86619736, compound

Participants

Reaction Steps

Sodium hydride (68.3 mg of a 60% dispersion in mineral oil, 1.71 mmol) followed by tert-butyl bromoacetate (0.189 mL, 1.28 mmol) was added to a solution of 1-tetrahydro-2H-thiopyran-4-yl-1,3-dihydro-2H-benzimidazol-2-one from Step B (200 mg, 0.854 mmol) in DMF (5 mL). After 1 h, the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (10 mL). The organic layer was washed with saturated NaHCO3 (5 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 50:50, gave the title compound. MS: m/z=349 (M+1).

Provenance & Evidence