Réaction #11067

Équation de réaction

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

Rendement 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

Rendement 90.0%

Solvants

EtOAc

CH2Cl2 DMF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine
2. 2
   SéchageThe mixture was dried (Na2SO4)
3. 3
   Concentrationconcentrated

Mode opératoire

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.

Source