Dichloromethane → HCID 10022833, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-[1-({4-[(hydroxyamino)carbonyl]phenoxy}-carbonyl)cyclohexyl]-benzoate (PX118926) (0.12 g, 0.27 mmol), dichloromethane (4 ml), and trifluoroacetic acid (1 ml) was stirred under argon atmosphere at room temperature until the starting material disappeared (ca. 2 hours). The mixture was supplemented with ethyl acetate (150 ml), the obtained solution was washed successively with water (2×100 ml), brine (50 ml), and dried (Na2SO4). The solvents were evaporated and the residue was chromatographed on silica gel with chloroform-isopropanol (9:1) as eluent to give the title compound in 48% yield as crystals, m.p. 169-170° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.18-2.05 (8H, m); 2.34-2.69 (2H, m, overlapped with a signal of DMSO); 7.05 (2H, d, J=8.5 Hz); 7.62 (2H, d, J=8.4 Hz); 7.78 (2H, d, J=8.5 Hz); 7.99 (2H, d, J=8.4 Hz); 9.09 (1H, br s); 11.26 (1H, br s). HPLC analysis on Chromasil 100 C18 column: impurities 5% (column size 4.6×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 254 nm; sample concentration 1.0 mg/ml; flow rate 1.5 ml/min). Anal. Calcd for C21H21NO6*0.25H2O, %: C, 65.02; H, 5.59; N, 3.61. Found, %: C, 64.88; H, 5.49; N, 3.45.

Provenance & Evidence