Triethylamine → HCID 9796787, compound

Participants

Reaction Steps

To a solution of [3-(3-phenyl-acryloylamino)-phenoxy]-acetic acid (9) (0.297 g, 1.0 mmol) in tetrahydrofuran (3 ml) at 0÷5° C. temperature (ice bath) triethylamine (0.18 ml, 1.3 mmol) followed by iso-butyl chloroformate (0.15 ml, 1.15 mmol) were added. The reaction mixture was stirred for 20 min. In another vessel, a mixture of hydroxylamine hydrochloride (0.122 g, 1.7 mmol) and sodium methoxide (0.095 mg, 1.75 mmol) was prepared. The both mixtures were combined and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate (20 ml) and the organic layer was washed successively with 1N KH2PO4, water, brine, and dried (Na2SO4). The solvent was partially removed until the formation of a precipitate started. The mixture was allowed to stand at room temperature for 6 hours. The precipitate was filtered and washed with diethyl ether to give the title compound (0.090 g, 30%). M.p. 163° C. (dec.). 1H NMR (DMSO-d6, HMDSO), δ: 4.45 (s, 2H); 6.60-6.73 (m, 1H); 6.83 (d, 1H, J=15.6 Hz); 7.18-7.30 (m, 2H); 7.36-7.51 (m, 4H); 7.53-7.68 (m, 3H); 8.98 (s, 1H); 10.23 (s,1H); 10.87 (s, 1H). HPLC analysis on Zorbax SB-C18 column: impurities ˜1% (column size 4.6×150 mm; mobile phase acetonitrile—0.1% H3PO4, gradient from 50:50 to 100:0; detector UV 270 nm; sample concentration 0.7 mg/ml, flow rate 1.0 ml/min). Anal. Calcd for C17H16N2O4: C, 65.38; H, 5.16, N 8.97. Found: C, 65.09, H, 5.14, N, 8.73.

Provenance & Evidence