Hydroxyamine hydrochloride → HCID 86746786, compound

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A solution of ethyl-4-formylamino-3-[3'-(N-tert-butyloxycarbonylamino)propionyl]benzoate (7.04 g, 20 mmol) and hydroxylamine hydrochloride (7.65 g, 110 mmol) in pyridine (200 ml), was heated at reflux for 15 hours. After this time the solution was cooled to ambient temperature and the solvent evaporated in vacuo. The residue was chromatographed (eluent 1:1 petrol:ethyl acetate) to give the title oxime (5.0 g, 71%) as a solid. m.p. 138°-140° C. NMR δ (250 MHz, CDCl3) 1.40 (12H, m), 3.13 (2H, t, J=7 Hz), 3.40 (2H, m), 4.31 (2H, q, J=7 Hz), 5.19 (1H, br s), 6.11 (2H, br s), 6.66 (1H, d, J=9 Hz), 7.73 (1H, dd, J=9 and 2 Hz), 8.10 (1H, br s), 10.46 (1H, br s).

Provenance & Evidence