Trifluoroacetic acid → Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

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Reaction Steps

Trifluoroacetic acid (3 ml) was added to a stirred solution of ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]- hexanoate (260 mg) dissolved in dichloromethane (3 ml). After 18 hours the solvents were removed in vacuo and the residual gum dissolved in dichloromethane. This solution was treated with a saturated solution of sodium hydrogen carbonate. The organic phase was washed with water, dried and evaporated. Trituration of the residue with hexane gave the title compound, 120 mg, as a white solid: m.p. 104°-106° C.; NMR (CDCl3) δ8.22(2H,d), 7.12(2H,d), 6.90(2H,d), 6.64(2H,dd), 5.82(1H,s), 4.13(2H,q), 3.97(2H,t), 2.34(2H,t), 1.80(2H,m), 1.70(2H,m), 1.53(2H,m), 1.27(3H,t); m/e 329 (M+H)+ ; calculated for C19H24N2O3.0.25H2O:C, 68.6; H, 7.4; N, 8.4. found: C, 68.8; H, 7.3; N, 8.2%.

Provenance & Evidence