Reaktion #11067

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 90.0%

Lösungsmittel

EtOAc

CH2Cl2 DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine
2. 2
   TrocknenThe mixture was dried (Na2SO4)
3. 3
   Einengenconcentrated

Vorschrift

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.

Quelle