Sodium Acetate → HCID 13606758, compound

HRID 1380105Notes

Reaction equation

HRID 1380105 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH3:21])=O)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:28][C:29]([O-:31])=[O:30].[Na+]>C(OC(=O)C)(=O)C>[CH2:25]([O:24][C:22]([C:5]1[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19][CH2:21][O:31][C:29](=[O:30])[CH3:28])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]=1[CH3:27])=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 13606757HCID 13606757, compound

Product 1

HCID 13606758HCID 13606758, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 3.31 g (8.46 mm) of sulfoxide 34 and NaOAc (anhydrous, 1.10 g) in 9.1 mL of acetic-anhydride was stirred at reflux for 40 minutes. The acetic anhydride was removed at reduced pressure, and the residue diluted with 250 mL of CH2CL2 and 50 mL of H2O. The organic portion was washed with 10% aqueous HCl, 5% aqueous NaHCO3, and brine, dried (anhydrous MgSO4), filtered, evaporated, and flash chromatographed (silica gel, 30% EtOAc in hexane) to give acetate 35 (1.60 g, 44%).

Workup

  1. temperatureat reflux for 40 minutes
  2. customThe acetic anhydride was removed at reduced pressure
  3. additionthe residue diluted with 250 mL of CH2CL2 and 50 mL of H2O
  4. washThe organic portion was washed with 10% aqueous HCl, 5% aqueous NaHCO3, and brine
  5. dry with materialdried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customflash chromatographed (silica gel, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-2bdea33c1f954cb5ab6c25d069a12f35
Source dataset
uspto-grants-1986_04
Patent number
US04579851

Reaction notes

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