Réaction #11086

Équation de réaction

Na2SO3

28c

(6S,8R)-allyl-[8-allyl-6-(tert-butoxycarbonyl-phenyl-aminocarbonyl)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl]-carbamic acid benzyl ester

H2O2

LiOH

→

28d

Rendement 96.0%

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

Rendement 96.0%

Solvants

H2O

THF H2O

Conditions de réaction

Traitement

1. 1
   AutreThe organic solvent was evaporated under a stream of nitrogen
2. 2
   FiltrationThe precipitate was filtered
3. 3
   Lavagerinsed with H2O and 0.1 N NaOH
4. 4
   Extractionextracted with EtOAc (3×)
5. 5
   ExtractionThe combined organic extract
6. 6
   Lavagewas washed with brine
7. 7
   Séchagedried (Na2SO4)
8. 8
   Concentrationconcentrated

Mode opératoire

To a solution of 28c (311 mg, 0.532 mmol) in 5 mL THF/H2O (4:1) at 0° C., were added 30% H2O2 (0.241 mL, 2.13 mmol) and IM LiOH (0.851 mL, 0.851 mmol). The mixture was stirred at 0° C. for 2 h, then Na2SO3 and 10 mL H2O were added. The organic solvent was evaporated under a stream of nitrogen. The precipitate was filtered and rinsed with H2O and 0.1 N NaOH. The combined aqueous filtrate was acidified with conc. HCl, then extracted with EtOAc (3×). The combined organic extract was washed with brine, dried (Na2SO4), and concentrated to afford 208 mg (96%) of 28d. MS (ESI) 410.3 (M+H+), 432.3 (M+Na+), 408.2 (M−H+).

Source