Reacción #57983

Ecuación de reacción

hydrochloric acid

hydroxylamine

NaOH

4-{2-[3-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]-ethoxy}-benzoate

→

title compound

N-hydroxy-4-{2-[3-(2,2,2-trifluoroethyloxymethyl)benzofuran-2-yl-carbonylamino]ethoxy}benzamide

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give pH 10-11
2. 2
   ConcentraciónThe reaction mixture was concentrated in vacuo
3. 3
   Otroto give a solid which
4. 4
   Otrowas collected
5. 5
   Lavadowashed with water
6. 6
   workup.DISSOLUTIONdissolved in acetonitrile
7. 7
   Otrowater and purified with prep HPLC

Procedimiento

4-{2-[3-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]-ethoxy}-benzoate was dissolved in MeOH and excess aqueous hydroxylamine solution and NaOH(aq) were added to give pH 10-11. After stirring overnight, the reaction mixture was neutralized reaction to pH 7-8 with aqueous hydrochloric acid. The reaction mixture was concentrated in vacuo to give a solid which was collected and washed with water, then dissolved in acetonitrile and water and purified with prep HPLC to give the title compound (35 mg). 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 8.95 (t, J=5.6 Hz, 1H), 8.89 (s, 1H), 7.81 (d, J=7.6 Hz, 1H), 7.70 (d, J=8.8 Hz, 2H), 7.63 (d, J=8.8 Hz, 1H), 7.50 (t, J=8.8 Hz, 1H), 7.36 (t, J=8.0 Hz, 1H), 7.00 (d, J=9.2 Hz, 2H), 5.25 (s, 2H), 4.18 (m, 4H), 3.67 (m, 2H). EM (calc.): 452.1; MS (ESI) m/e (M+1H)+: 453.0, (M−1H)−: 451.0.

Fuente