Ethyl 4-(4-nitro-3-phenyl-butyrylamino)benzoate → Ethyl 4-(3-naphthalen-2-yl-4-nitro-butyrylamino)benzoate

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Reaction Steps

This was prepared from corresponding amide 42 (0.995 g, 2.88 mmol) in a similar manner as described for preparation of 47. Chromatography on silica gel performed using a FlashMaster 3 purification station (75:25 hexanes/ethyl acetate, Rf 0.20) afforded 48 (0.819 g, 2.017 mmol, 70%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 1.26 (3H, t, J 7.6 Hz), 2.85-2.93 (2H, m), 4.10 (1H, quint, J 8.0 Hz), 4.23 (1H, q, J 7.2 Hz), 5.02-5.10 (2H, m), 7.45-7.48 (2H, m), 7.54 (1H, dd, J 1.6, 8.8 Hz), 7.62 (2H, d, J 8.8 Hz), 7.82-7.87 (6H, m). 13C NMR (400 MHz, CDCl3) δ 14.52, 40.75, 40.79, 61.21, 79.48, 119.21, 124.97, 126.43, 126.65, 126.78, 126.87, 127.92, 128.04, 129.37, 130.94, 133.11, 133.59, 135.89, 141.68, 166.37, 168.54. MS (API-ES): m/z found 407 [M+H]+ (100%), HRMS (API-ES) m/z 407.1607 [M+H]+.

Provenance & Evidence