Pyridine → Tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate

Participants

Reaction Steps

To a mixture of tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride (600 mg, 1.90 mmol) in CH2Cl2 were added pyridine (0.38 mL, 4.75 mmol) and acetyl chloride (0.20 mL, 2.85 mmol). After stirring for 2 h at room temperature, the reaction mixture was diluted with EtOAc, washed (sat. CuSO4, sat. NaHCO3, brine), dried (MgSO4), and concentrated. Flash chromatography on silica gel (50-100% EtOAc/hexanes) afforded tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate as a thick, colorless oil. 1H NMR (CDCl3) δ7.94 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.2 Hz, 2H), 5.87 (t, J=5.5 Hz, 1H), 3.96 (dd, J=8.8, 5.9 Hz, 1H), 3.71-3.60 (m, 2H), 3.67 (s, 3H), 1.93 (s, 3H), 1.57 (s, 9H). MS (ESI) calcd [M+H]+ 322.1, found 322.1.

Provenance & Evidence