Sodium Carbonate → HCID 67674094, compound

HRID 1585509Notes

Reaction equation

HRID 1585509 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C@@H:8]1[C:11](=[O:12])[N:10](CC2C=CC(OC)=CC=2OC)[C@@H:9]1[CH2:24][CH2:25][C:26](=[O:36])[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])([CH3:4])([CH3:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[C:1]([O:5][C:6](=[O:37])[NH:7][C@@H:8]1[C:11](=[O:12])[NH:10][C@@H:9]1[CH2:24][CH2:25][C:26](=[O:36])[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24412Potassium PersulfateHCID 67673869HCID 67673869, compound

Product 1

HCID 67674094HCID 67674094, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 830 g (1.50 Mol) (2R, 3S)-[2-[4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-butyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-3-yl]-carbamic acid tert-butyl ester (4) in 8.3 l acetonitrile and 4.15 l water were added in intervals of 25 min three portions of 415 g (1.53 Mol) potassium persulfate at 72-75° C. The pH was kept at 4.9-5.3 by addition of a 10% solution of sodium carbonate (3.75 l). The mixture was stirred at the indicated temperature for 2 h and then cooled to room temperature. The solids were removed by filtration and washed with 5.6 l ethyl acetate. The filtrates were thoroughly mixed. The phases were separated and to the organic layer was added 2.54 l sodium bisulfite 40% in water. The phases were thoroughly mixed, cooled to 5-0° C., stirred for 1 h. The solids were removed by filtration and washed with 0.62 l ethyl acetate. The combined filtrates were stirred and the phases were allowed to separate. The organic phase was consecutively washed with aqueous solutions of 1.86 l sodium chloride (10%), 1.86 l sodium carbonate (5%) and twice with 1.86 l sodium chloride (10%), dried over 1.15 kg sodium sulfate and filtered. The solids were washed with 1.25 l ethyl acetate. To the combined filtrates was added 1.25 kg silica gel 60 (230-400 mesh) and the mixture was concentrated under aspirator vacuum. The remaining solid was charged onto a column containing 3.5 kg silica gel 60 (230-400 mesh). The product was eluted with a gradient of n-hexane:ethyl acetate=2:1 to 1:2. The pure product containing fractions were combined and concentrated under aspirator vacuum and dried 0,1 torr at 45° C. to yield 464 g (2R, 3S)-[2-[4-(tert-butyl dimethyl-silanyloxy)-3-oxo-butyl]-4-oxo-azetidin-3-yl]-carbamic acid tert-butyl ester (5) as a yellow amorphous solid (80% Th.).

Workup

  1. customThe solids were removed by filtration
  2. washwashed with 5.6 l ethyl acetate
  3. additionThe filtrates were thoroughly mixed
  4. customThe phases were separated and to the organic layer
  5. additionwas added 2.54 l sodium bisulfite 40% in water
  6. additionThe phases were thoroughly mixed
  7. temperaturecooled to 5-0° C.
  8. stirringstirred for 1 h
  9. customThe solids were removed by filtration
  10. washwashed with 0.62 l ethyl acetate
  11. stirringThe combined filtrates were stirred
  12. customto separate
  13. washThe organic phase was consecutively washed with aqueous solutions of 1.86 l sodium chloride (10%), 1.86 l sodium carbonate (5%) and twice with 1.86 l sodium chloride (10%)
  14. dry with materialdried over 1.15 kg sodium sulfate
  15. filtrationfiltered
  16. washThe solids were washed with 1.25 l ethyl acetate
  17. additionTo the combined filtrates was added 1.25 kg silica gel 60 (230-400 mesh)
  18. concentrationthe mixture was concentrated under aspirator vacuum
  19. additionThe remaining solid was charged onto a column
  20. additioncontaining 3.5 kg silica gel 60 (230-400 mesh)
  21. washThe product was eluted with a gradient of n-hexane
  22. additionThe pure product containing fractions
  23. concentrationconcentrated under aspirator vacuum
  24. customdried 0,1 torr at 45° C.

Sources & evidence

ORD record
ord-647a4eb03d884f638cd6ea42c7482884
Source dataset
uspto-grants-1999_08
Patent number
US05939410

Reaction notes

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