Water → HCID 21964005, compound

HRID 2212371Notes

Reaction equation

HRID 2212371 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C:15]1([S:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:20][CH2:19][CH:18]([CH2:21][S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:17][CH2:16]1.[OH2:42]>C(OCC)(=O)C.[Ru](=O)=O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C:15]1([S:29]([C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=2)(=[O:31])=[O:30])[CH2:20][CH2:19][CH:18]([CH2:21][S:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)(=[O:2])=[O:42])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 962WaterHCID 21963975HCID 21963975, compoundHCID 23667635Sodium periodate

Product 1

HCID 21964005HCID 21964005, compound

Reagents, catalysts & solvents 2

HCID 82848Ruthenium dioxideCatalystHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of sodium periodate (223 mg, 1 mmol) in ethyl acetate (2 mL) and water (4 mL) was added ruthenium dioxide (5 mg), followed by the product from Example 78 (250 mg, 0.47 mmol) in ethyl acetate (2 mL). After 30 mins the reaction was diluted with ethyl acetate, filtered through Celite® and the water layer from the filtrate removed. The organic layer was dried (MgSO4), evaporated, and the residue purified by flash chromatography on silica eluting with iso-hexane/ethyl acetate (1:1) to give a white solid (220 mg).

Workup

  1. filtrationfiltered through Celite®
  2. customthe water layer from the filtrate removed
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customthe residue purified by flash chromatography on silica eluting with iso-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-53207aba167946809622f82b6bfc7a7b
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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