Reacción #158012

Ecuación de reacción

(R)-ethyl 4-(3′-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate

Et3N

Ac2O

→

(R)-ethyl 4-(3′-acetamidobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate

Rendimiento 92.0%

Disolventes

DCM

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe products are extracted with DCM in a phase separator
2. 2
   Concentraciónconcentrated
3. 3
   Otroto give crude (98 mg)
4. 4
   OtroThe crude is purified by silica gel flash column chromatography (eluent: DCM/MeOH=10:1)

Procedimiento

A solution of (R)-ethyl 4-(3′-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (70.5 mg, 0.171 mmol), Et3N (0.027 ml, 0.205 mmol) and Ac2O (0.019 ml, 0.205 mmol) in DCM (1.7 ml) is allowed to stir at room temperature for 65 hours. The reaction mixture is diluted with water. The products are extracted with DCM in a phase separator and concentrated to give crude (98 mg). The crude is purified by silica gel flash column chromatography (eluent: DCM/MeOH=10:1) to give (R)-ethyl 4-(3′-acetamidobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (71.5 mg); HPLC retention time=1.45 minutes (condition D); MS (m+1)=455.4; 1H NMR (400 MHz, CD3CN, mixture of rotamers, data for major rotamer) δ ppm 1.21 (t, J=7.1 Hz, 3 H) 2.07 (s, 3 H) 2.31-2.34 (m, 2 H) 2.40-2.51 (m, 4 H) 2.82-2.84 (m, 2 H) 3.58 (s, 3 H) 4.07 (q, J=7.1 Hz, 2 H) 4.34-4.43 (m, 1 H) 6.46 (br d, J=8.9 Hz, 1 H) 7.28-7.39 (m, 4 H) 7.52-7.54 (m, 3 H) 7.80 (s, 1 H) 8.37 (br s, 1 H).

Fuente