Hydrogen Peroxide → (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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 18e (480 mg, 0.800 mmol) in 10 mL THF/H2O (4:1) at 0° C., was added 30% H2O2 (1.28 mL, 11.3 mmol) and IN LiOH (1.28 mL, 1.28 mmol). The mixture was stirred at 0° C. of 45 min, then Na2SO3 (1.51 g, 12 mmol) was added. The mixture was stirred 30 min, then evaporated in vacuo. The residue was diluted with Et2O and extracted with 0.1 N NaOH (3×). The combined aqueous was acidified to pH 3 with conc. HCl, then was extracted with EtOAc (5×). The combined organic extract was washed with brine, dried (Na2SO4) and concentrated to afford 272 mg (80%) of a acid 18f, which was used in the following step with out further purification. MS (ESI) 447.3 (M+Na+), 423.2 (M−H+).

Herkunft & Nachweise