4-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate → 4-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl)-cyclohexanecarboxylate

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A mixture of 4-{[(benzyloxy)amino]carbonyl]phenyl 1-(4-methoxyphenyl) cyclohexanecarboxylate (22a) (0.072 g, 0.16 mmol) and 5% palladium on activated carbon (0.054 g) in methanol (1 ml) was hydrogenated at room temperature until the starting material disappeared (ca. 45 minutes). The black suspension was filtered, the catalyst was washed with methanol (3×1 ml), and the filtrate was evaporated to give a white solid. The solid was suspended in diethyl ether (3 ml) and the mixture was intensively stirred overnight. The solid was filtered, washed with diethyl ether (1 ml), and dried in vacuum to give the title compound (0.037 g, 64%) as white crystals, m.p. 127-129° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.18-1.90 (8H, m); 2.36-2.65 (2H, m, overlapped with a signal of DMSO); 3.76 (3H, s); 6.97 (2H, d, J=8.6 Hz); 7.01 (2H, d, J=8.8 Hz); 7.40 (2H, d, J=8.8 Hz); 7.77 (2H, d, J=8.6 Hz); 9.07 (1H, br s); 11.23 (1H, br s). HPLC analysis on Symmetry C8 column: impurities 2.2% (column size 3.9×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 230 nm; sample concentration 0.3 mg/ml; flow rate 1.0 ml/min). Anal. Calcd for C21H23NO5*0.3H2O, %: C, 67.29; H, 6.35,; N, 3.74. Found, %: C, 67.29; H, 6.23; N, 3.76.

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