Potassium Carbonate → [2-(t-Butoxycarbonylmethyl-amino)-phenyl]-acetic acid methyl ester

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Reaction Steps

The title B compound, (2-amino-phenyl) acetic acid methyl ester (4.2 g, 25.4 mmol) is dissolved in DMF (30 mL). Powdered potassium carbonate (8.78 g, 63.5 mmol) and t-butyl bromoacetate (4.12 mL, 27.9 mmol) are added and the reaction is stirred at room temperature for 18 h and then at 50° C. for 1 h. The reaction is diluted with water (300 mL) and extracted with EtOAc (2×200 mL). Combined EtOAc layers are washed with water (2×100 mL) then brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated to give a viscous brown oil. This residue is chromatographed on a 110 g silica gel RediSep (Isco Inc.) column with a 30 mL/min gradient elution of 10:90 (EtOAc:hexane) to 25:75 over 30 min. Fractions containing product are combined and evaporated to yield [2-(t-butoxy-carbonylmethyl-amino)-phenyl]-acetic acid methyl ester as a clear amber oil: [M+1]+=280.

Provenance & Evidence