Reacción #2015

Ecuación de reacción

BOP

D-Tryptophan allyl ester

triethylamine

N-benzyloxycarbonyl-α-methylalanine

→

desired product

Rendimiento 84.5%

(R)-α-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

Rendimiento 84.5%

Disolventes

—

hexanes

ethyl acetate

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction quenched with saturated brine (5 ml)
2. 2
   OtroThe methylene chloride layer was separated
3. 3
   Secadodried with magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otrothe volatiles removed under reduced pressure
6. 6
   Otroto leave a dark brown oil

Procedimiento

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

Fuente