Réaction #11066

Équation de réaction

Na2SO3

LiOH

18e

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

H2O2

→

acid 18f

Rendement 80.1%

(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

Rendement 80.1%

Solvants

THF H2O

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred 30 min
2. 2
   Autreevaporated in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with Et2O
4. 4
   Extractionextracted with 0.1 N NaOH (3×)
5. 5
   Extractionwas extracted with EtOAc (5×)
6. 6
   ExtractionThe combined organic extract
7. 7
   Lavagewas washed with brine
8. 8
   Séchagedried (Na2SO4)
9. 9
   Concentrationconcentrated

Mode opératoire

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+).

Source