Reacción #11067

Ecuación de reacción

18f

(6S,8R)-3-(allyl-benzyloxycarbonyl-amino)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

[(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester

HOAT

NaHCO3

EDCI

→

intermediate

Rendimiento 90.0%

(6S,8R)-allyl-{8-azido-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester

Rendimiento 90.0%

Disolventes

EtOAc

CH2Cl2 DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine
2. 2
   SecadoThe mixture was dried (Na2SO4)
3. 3
   Concentraciónconcentrated

Procedimiento

To a solution of 18f (270 mg, 0.636 mmol) and [(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (272 mg, 0.763 mmol) in 6 mL CH2Cl2/DMF (5:1) at 0° C., were added HOAT (95 mg, 0.700 mmol), NaHCO3 (187 mg, 2.23 mmol), and EDCI (171 mg, 0.890 mmol). The mixture was allowed to warm to rt and stir for 15 h. The mixture was diluted with EtOAc, washed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine. The mixture was dried (Na2SO4) and concentrated to afford 393 mg (90%) of intermediate 18 g.

Fuente