Sodium periodate → HCID 86614493, compound

HRID 639708Notes

Reaction equation

HRID 639708 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[N:5]([C:14]1[CH:19]=[C:18]([CH:20]=C)[N:17]=[C:16]([NH2:22])[C:15]=1[N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2].I([O-])(=O)(=O)=[O:28].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4](=[O:26])[N:5]([C:14]1[CH:19]=[C:18]([CH:20]=[O:28])[N:17]=[C:16]([NH2:22])[C:15]=1[N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67457433HCID 67457433, compound

Product 1

HCID 86614493HCID 86614493, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

(2-Amino-3-nitro-6-vinyl-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (270 mgs/0.755 mmols) was dissolved in acetone (5 mls)/water (5 mls) and osmium tetroxide (2.5% wt in tBuOH) (0.10 mls/0.008 mmols) was added. Stirred for 5 mins to give brown solution then added sodium metaperiodate (500 mgs/3.47 mmols). Orange suspension stirred for 1 hour. Partitioned between EtOAc (100 mls) and sodium thiosulfate pentahydrate (20% wt in H2O) (50 mls). Organic collected, washed with brine, dried over Na2SO4, filtered and concentrated to a brown resin. Purification by column chromatography eluting with EtOAc gave the title compound (220 mgs) as a yellow oil.

Workup

  1. additionwas added
  2. customto give brown solution
  3. stirringOrange suspension stirred for 1 hour
  4. customPartitioned between EtOAc (100 mls) and sodium thiosulfate pentahydrate (20% wt in H2O) (50 mls)
  5. washOrganic collected, washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to a brown resin
  9. customPurification by column chromatography
  10. washeluting with EtOAc

Sources & evidence

ORD record
ord-673dcfc2071c457ab646ce748d6216ab
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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