Water → HCID 18429230, compound

HRID 383051Notes

Reaction equation

HRID 383051 reaction equation
[CH2:1]([N:4]([C:28](=[O:39])[CH:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:30][O:31][C:32](=[O:34])[CH3:33])[C:5]1[C:6]([I:27])=[C:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C:8]([I:21])=[C:9]([C:19]=1[I:20])[C:10]([NH:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[O:11])[CH:2]=[CH2:3].[OH2:40].C([O:45]O)(C)(C)C.C[N+]1([O-])CCOCC1>CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:40][CH:2]([CH2:3][OH:45])[CH2:1][N:4]([C:28](=[O:39])[CH:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:30][O:31][C:32](=[O:34])[CH3:33])[C:5]1[C:6]([I:27])=[C:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C:8]([I:21])=[C:9]([C:19]=1[I:20])[C:10]([NH:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 82029Methyl morpholine oxideHCID 18429363HCID 18429363, compound

Product 1

HCID 18429230HCID 18429230, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

5-[N′-(2-Propenyl)-2,3 -diacetoxypropionylamino]-3-acetoxymethyl-N-(2-acetoxyethyl)-2,4,6-triiodobenzamide (8.73 g, 9.90 mmol) was dissolved in acetone (360 ml) and water (40 ml) and the solution was cooled in an ice-bath. Osmium tetroxide (110 mg, 0.43 mmol), and an excess of t-butylhydroperoxide was added. 4-Methyl-morpholine N-oxide (2,32 g, 19.8 mmol) was added and the mixture was stirred at room temperature for 24 h. The reaction was then quenched by addition of a saturated solution of sodium hydrogen sulphite (120 ml). The acetone was evaporated, and the residue was extracted with ethyl acetate (2×70 ml). The organic extracts were washed with water (50 ml), dried (Na2SO4), and the solvent was evaporated. The residue was chromatographed on a column of silica using a mixture of ethyl acetate/acetone (1/1) as the eluent.Yield: 5.82 g (64%).

Workup

  1. customThe reaction was then quenched by addition of a saturated solution of sodium hydrogen sulphite (120 ml)
  2. customThe acetone was evaporated
  3. extractionthe residue was extracted with ethyl acetate (2×70 ml)
  4. washThe organic extracts were washed with water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed on a column of silica using
  8. additiona mixture of ethyl acetate/acetone (1/1) as the eluent

Sources & evidence

ORD record
ord-93dbe4c049da472da354d5583fb95d88
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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