Reacción #158011

Ecuación de reacción

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

→

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

Rendimiento 91.6%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture is filtered
2. 2
   Concentraciónthe solution is concentrated

Procedimiento

A suspension of (R)-ethyl 3-(4-methoxy-4-oxobutanamido)-4-(3′-nitrobiphenyl-4-yl)butanoate (123 mg, 0.278 mmol) and Pd/C (59.2 mg, 0.028 mmol) in EtOH (2 ml) is allowed to stir under hydrogen at room temperature for 5.5 hours. The reaction mixture is filtered, and the solution is concentrated to give (R)-ethyl 4-(3′-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (105 mg); HPLC retention time=0.84 minutes (condition B); MS (m+1)=413.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (t, J=7.2 Hz, 3 H) 2.41-2.65 (m, 6 H) 2.85-3.00 (m, 2 H) 3.67 (s, 3 H) 4.11-4.22 (m, 2 H) 4.46-4.54 (m, 1 H) 6.31 (br d, J=8.8 Hz, 1 H) 6.71-6.74 (m, 1 H) 6.95-7.02 (m, 2 H) 7.21-7.25 (m, 3 H) 7.48-7.50 (m, 2 H).

Fuente