4-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl)-cyclohexanecarboxylate → 4-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl)-cyclopentanecarboxylate

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The title compound was obtained from 4-{(benzyloxy)[(benzyloxy)imino] methyl}phenyl 1-(4-methoxyphenyl)-cyclopentanecarboxylate (26) by a method analogous to that described for 4-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl) -cyclohexanecarboxylate (PX118478), using dioxane as a solvent. After filtration of the catalyst and evaporation of the solvent the crude product was washed with diethyl ether to give the title compound in 78% yield as crystals, m.p. 143-144° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.61-1.86 (4H, m); 1.86-2.08 (2H, m); 2.54-2.74 (2H, m); 3.75 (3H, s); 6.95 (2H, d, J=8.7 Hz); 7.01 (2H, d, J=8.5 Hz); 7.38 (2H, d, J=8.7 Hz); 7.75 (2H, d, J=8.5 Hz); 9.04 (1H, s); 11.22 (1H, s). HPLC analysis on Alltima C18 column: impurities 2% (column size 4.6×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 50:50; detector UV 230 nm; sample concentration 1.0 mg/ml; flow rate 1.5 ml/min). Anal. Calcd for C20H21NO5*0.1 EtOAc, %: C, 67.28; H, 6.03; N, 3.85. Found, %: C, 67.00; H, 5.96; N, 3.78.

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