Reacción #2011

Ecuación de reacción

BOP

amine

D-Homophenylalanine allyl ester

triethylamine

N-carbobenzyloxy-2-methylalanine

→

desired product

Rendimiento 69.7%

(R)-α-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl ester

Rendimiento 69.7%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe resultant homogenous yellow solution quenched by addition of brine
2. 2
   ExtracciónThe two phase system was extracted with methylene chloride (2×25 ml)
3. 3
   Secadothe combined methylene chloride layers dried
4. 4
   FiltraciónFiltration of the methylene chloride solution
5. 5
   Otroto remove the
6. 6
   Otrospent drying agent
7. 7
   Otrofollowed by evaporation of solvent
8. 8
   Otroafforded an oil which
9. 9
   Otrowas purified by column chromatography on silica gel using
10. 10
    workup.ADDITIONa solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant

Procedimiento

The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultant homogenous yellow solution quenched by addition of brine. The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride layers dried over powdered anhydrous magnesium sulfate. Filtration of the methylene chloride solution to remove the spent drying agent followed by evaporation of solvent afforded an oil which was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant. The desired product (419 mg; 69.7%) was isolated as a white amorphous solid. FAB-MS:- calculated for C25 H30N2O5 438.2; found 439.3 (M+1).

Fuente