Sodium periodate → HCID 69972743, compound

HRID 2296654Notes

Reaction equation

HRID 2296654 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][N:11]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C@@H:10]([CH2:29][OH:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:32].[Na+]>CC(C)=O.O.O.[Ru](=O)=O>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][N:11]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C@@H:10]([C:29]([OH:32])=[O:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 54432397HCID 54432397, compound

Product 1

HCID 69972743HCID 69972743, compoundYield 102.4%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ruthenium (IV) oxide hydrate (238 mg) was added to a solution of (2R,5R)-4-(tert-butoxycarbonyl)-2-hydroxymethyl-1-(4-methoxybenzenesulfonyl)-5-(2-methylpropyl)piperazine (5.3 g) in acetone (50 ml) and H2O (20 ml), followed by addition of sodium periodate (5.1 g) with cooling on an ice bath. After stirring at the same temperature for 40 minutes, the reaction was quenched with 2-propanol (50 ml). Insoluble matter was removed by filtration through a celite pad, and the filtrate was washed with acetone and AcOEt. The filtrate and combined washings were concentrated in vacuo, and the residue was partitioned by dissolving same in 5% aqueous sodium bisulfite and AcOEt. The organic layer was washed with saturated NaCl solution, dried over MgSO4, and concentrated in vacuo to give 5.6 g of (2R,5R)-4-(tert-butoxycarbonyl)-1-(4-methoxybenzenesulfonyl)-5-(2-methylpropyl)piperazine-2-carboxylic acid as an amorphous powder.

Workup

  1. temperaturewith cooling on an ice bath
  2. customthe reaction was quenched with 2-propanol (50 ml)
  3. customInsoluble matter was removed by filtration through a celite pad
  4. washthe filtrate was washed with acetone and AcOEt
  5. concentrationwere concentrated in vacuo
  6. customthe residue was partitioned
  7. dissolutionby dissolving same in 5% aqueous sodium bisulfite
  8. washThe organic layer was washed with saturated NaCl solution
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8274321a33564105a74d3c50c3da8f19
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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