Potassium Carbonate → HCID 91490383, compound

HRID 1357518Notes

Reaction equation

HRID 1357518 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(O[C@H:16]1[C@H:21]([O:22][Si](C(C)(C)C)(C)C)[CH2:20][C:19]([C:30]([O:32][CH3:33])=[O:31])=[CH:18][C@@H:17]1[CH2:34][CH:35]=[CH2:36])(=O)C1C=CC=CC=1.CS(Cl)(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CO.ClCCl.C1COCC1.C(OCC)(=O)C>[CH2:34]([C@@H:17]1[C@H:16]2[C@H:21]([O:22]2)[CH2:20][C:19]([C:30]([O:32][CH3:33])=[O:31])=[CH:18]1)[CH:35]=[CH2:36]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 70019627HCID 70019627, compound

Product 1

HCID 91490383HCID 91490383, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate can be added to a room temperature solution of Example 18E in methanol and stirred over night. The reaction mixture can then be filtered, concentrated, and purified to yield the first intermediate compound. Methanesulfonyl chloride can then be added to a 0° C. solution of the first intermediate in dichloromethane. After stirring for up to 12 hours, the reaction mixture can then be washed with saturated NaHCO3, dilute citric acid solution, water, and brine, dried (MgSO4), filtered and concentrated. The concentrate can then be purified to afford the second intermediate. Tetrabutylammonium fluoride can then be added to a room temperature solution of the second intermediate in THF. After stirring for up to 12 hours, the reaction mixture can be diluted with ethyl acetate, washed with water, and brine, dried (MgSO4), filtered and concentrated and purified to afford the desired product.

Workup

  1. filtrationThe reaction mixture can then be filtered
  2. concentrationconcentrated
  3. custompurified
  4. customto yield the first intermediate compound
  5. stirringAfter stirring for up to 12 hours
  6. washthe reaction mixture can then be washed with saturated NaHCO3, dilute citric acid solution, water, and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. concentrationThe concentrate can
  11. customthen be purified
  12. customto afford the second intermediate
  13. stirringAfter stirring for up to 12 hours
  14. washwashed with water, and brine
  15. dry with materialdried (MgSO4)
  16. filtrationfiltered
  17. concentrationconcentrated
  18. custompurified

Sources & evidence

ORD record
ord-57b359b0dc084925a00ab981a9d606c1
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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