Reacción #163221

Ecuación de reacción

3-aminopropionic acid ethyl ester

Et3N

(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid

HATU

iPr2NEt

→

title compound

Rendimiento 113.0%

3-[2-(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetylamino]-propionic acid ethyl ester

Rendimiento 113.0%

Disolventes

EtOAc

Water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónto extract
2. 2
   LavadoThe organic layer is washed with brine
3. 3
   Secadodried with Na2SO4
4. 4
   Concentraciónconcentrated

Procedimiento

To a solution of 3-aminopropionic acid ethyl ester (41 mg, 0.268 mmol) and Et3N (0.082 mL, 0.730 mmol) is added a solution of (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid (100 mg, 0.243 mmol) in DMF (4 mL), HATU (102 mg, 0.268 mmol) and iPr2NEt (0.127 mL, 0.73 mmol). The reaction mixture is allowed to stir at ambient temperature for 18 h. Water is added and EtOAc is used to extract. The organic layer is washed with brine, dried with Na2SO4 and concentrated to give the title compound (140 mg) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.13 (m, 2H) 1.18 (t, J=7.07 Hz, 3H) 1.38-1.50 (m, 2H) 1.71 (dd, J=7.71, 4.17 Hz, 1H) 1.78 (t, J=12.63 Hz, 4H) 1.98 (d, J=6.57 Hz, 2H) 2.44 (t, J=6.82 Hz, 2H) 3.25-3.28 (m, 2H) 4.06 (q, J=7.07 Hz, 2H) 6.99 (ddd, J=7.89, 1.96, 1.01 Hz, 1H) 7.27-7.35 (m, 1H) 7.29 (d, J=8.59 Hz, 2H) 7.40 (s, 1H) 7.50 (d, J=8.34 Hz, 1H) 7.47-7.52 (m, 1H) 7.85 (t, J=2.02 Hz, 1H) 7.88 (t, J=5.81 Hz, 1H) 10.52 (s, 1H); (M+H)+510.2.

Fuente