Water → HCID 54162109, compound

Participants

Reaction Steps

To a stirred solution of ethyl-4-amino-3-[3'-(N-tert-butyloxycarbonylamino)-1'-hydroxyiminopropyl]benzoate (4.8 g, 14 mmol) and dimethylamino pyridine (1.67 g, 14 mmol) in dichloromethane (200 ml) was added acetic anhydride (1.3 ml, 14 mmol), under an atmosphere of nitrogen. After 2 hours the solution was poured into water (200 ml) and partitioned. The organic layer was separated, washed once more with water (200 ml), then the combined organic phases dried (MgSO4). The solvent was removed in vacuo, to afford an oily solid. Ether (200 ml) was added, and the mixture evaporated in vacuo once more to give a white solid. The solid was taken up in more ether (100 ml) and filtered off, to afford the title compound (4.4 g, 82%) as a white solid. m.p. 130°-135° C. NMR δ (250 MHz, CDCl3) 1.40 (12H, m), 2.27 (3H, s), 3.18 (2 H, t, J=7 Hz), 3.43 (2H, m), 4.33 (2H, q, J=7 Hz), 4.70 (1H, br s), 6.69 (1H, d, J=9 Hz), 7.82 (1H, dd, J=9 and 2 Hz), 8.17 (1H, br s).

Provenance & Evidence