Sodium periodate → HCID 69972743, compound

HRID 2271004Notes

Reaction equation

HRID 2271004 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 MgS04, 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. customdried over MgS04
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e7a73dc37634cedb71a6c672b18acb3
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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