Reacción #336812

Ecuación de reacción

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

acid 36

6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

2-t-butoxycarbonylamino-ethylamine

→

desired product ( 37 )

Rendimiento 73.0%

{2-[5-(2-tert-Butoxycarbonylaminoethylcarbamoyl)-pentylcarbamoyl]ethyl}-carbamic acid benzyl ester

Rendimiento 73.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe compound 37 was prepared
2. 2
   OtroRecrystallization of the crude product from EtOAc

Procedimiento

The compound 37 was prepared using General Procedure B with the acid 36 2.23 g, 6.63 mmol), 2-t-butoxycarbonylamino-ethylamine (1.27 g, 7.95 mmol), 1-hydrobenzotriazole (HOBt) (1.25 g, 9.28 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (1.79 g, 9.28 mmol) in DMF (20 mL). Recrystallization of the crude product from EtOAc afforded 2.30 g (73%) of the desired product (37) as a white solid. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.44 (s, 1H, NH), 6.23 (s, 1H, NH), 5.67 (s, 1H, NH), 5.19 (s, 1H, NH), 5.06 (s, 2H, OCH2Ar), 3.45 (dt, J=6.4, 12.4 Hz, 2H, CH2NHCO), 3.31 (dt, J=5.2, 10.4 Hz, 2H, CH2NHCO), 3.21 (m, 4H, CH2NHCO), 2.39 (dt, J=6.0, 6.4 Hz, 2H, CH2CO), 2.14 (dt, J=7.0, 7.2 Hz, 2H, CH2CO), 1.60 (m, 2H, CH2), 1.47 (m, 2H, CH2), 1.41 (s, 9H, t-Bu), 1.30 (m, 2H, CH2); ESI-MS m/z 513[N+Cl]−; 501[M+Na]+, 479[M+H]+.

Fuente