Sodium hydride → tert-Butyl (5,7-dimethyl-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate

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Reaction Steps

To a stirred solution of 5,7-dimethyl-2-benzoxazolinone (200 mg, 1.23 mmol, described in Intermediate 24) in DMF (2 mL) was added sodium hydride (59 mg of a 60% dispersion in mineral oil, 1.47 mmol). The mixture was stirred at ambient temperature for 10 min, then tert-butyl bromoacetate (287 mg, 1.47 mmol) was added and stirring was continued for 2 h. The reaction mixture was quenched with H2O and purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=222 (M−C4H7).

Provenance & Evidence