Ethyl Acetate → HCID 136018654, compound

Participants

Reaction Steps

To a mixture of 2-{benzyl-[2-(3-methyl-isoxazol-5-yl)-acetyl]-amino}-5-chloro-benzoic acid benzyl ester (3.30 g, 7.58 mmol) in 25 ml of DMF at 0° C. was added NaH (340 mg). The mixture was stirred at rt for 1 h under Ar. Treated with 200 ml of EtOAc, the mixture was extracted with H2O (4×50 ml). The combined aqueous layers were neutralized to pH=6 with 1N HCl and extracted with EtOAc (4×50 ml). The combined org. layers were washed with H2O (2×50 ml), brine (50 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure gave. 2.35 g (92%) of product as a white solid: 1H-NMR (CD3OD, 400 MHz) δ 9.49 (s, 1H), 8.21 (d, 1H, J=2.6 Hz), 7.48 (dd, 1H, J=9.0, 2.6 Hz), 7.17-7.36 (m, 7H), 5.60 (s, 2H), 2.43 (s, 3H), 2.54 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C20H15ClN203, 367.1 (M+H), found 367.0.

Provenance & Evidence