Sulfuric Acid → HCID 10999783, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL flask, 4-oxo-3-(3-phenyl-propionylamino)-pentanoic acid methyl ester (10 g, 36 mmol), and acetic anhydride (28 mL) were combined. Following addition of concentrated H2SO4 (1 mL), the solution was heated to 90° C. for 30 min and then cooled to ambient temperature. The reaction was slowly diluted with DI water (30 mL, potential exotherm). The reaction mixture was partitioned between CH2Cl2 and water. The organic phase was washed with DI water, 10% NaHCO3 (aq), brine (150 mL), and then dried over MgSO4 and concentrated to obtain a brown oil. The residue was purified by column chromatography (600 mL SiO2, 35% EtOAc/hexanes) to provide the desired product (3.25 g) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 3.72 (s, 3H), 3.47 (s, 2H), 3.08-2.96 (m, 4H), 2.24 (s, 3H); MS (EI+) 260 (M+H).

Provenance & Evidence