Réaction #2332

Équation de réaction

Trifluoroacetic acid

ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]-phenoxy]hexanoate

→

title compound

Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreAfter 18 hours the solvents were removed in vacuo
2. 2
   workup.DISSOLUTIONthe residual gum dissolved in dichloromethane
3. 3
   workup.ADDITIONThis solution was treated with a saturated solution of sodium hydrogen carbonate
4. 4
   LavageThe organic phase was washed with water
5. 5
   Autredried
6. 6
   Autreevaporated

Mode opératoire

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) δ 8.22 (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 C19 H24N2O3. 0.25H2O:C, 68.6; H, 7.4; N, 8.4. found: C, 68.8; H, 7.3; N, 8.2%.

Source