(7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethyloxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine → (7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylsulphinylethoxy)-9phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 1934370Notes

Reaction equation

HRID 1934370 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1[N:9]=[C:10]2[C:19]3[NH:18][C@H:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C@@H:16]([OH:26])[C@H:15]([O:27][CH2:28][CH2:29][S:30][CH3:31])[C:14]=3[CH:13]=[CH:12][N:11]2[C:32]=1[CH3:33]>O.CO>[CH3:7][C:8]1[N:9]=[C:10]2[C:19]3[NH:18][C@H:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C@@H:16]([OH:26])[C@H:15]([O:27][CH2:28][CH2:29][S:30]([CH3:31])=[O:2])[C:14]=3[CH:13]=[CH:12][N:11]2[C:32]=1[CH3:33]

Participants

5

Reactant 2

HCID 9929931(7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethyloxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridineHCID 23667635Sodium periodate

Product 1

HCID 10150757(7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylsulphinylethoxy)-9phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridineYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

130 mg of sodium metaperiodate, dissolved in 1 ml of water, is added to a solution of 200 mg of (7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridine in 5 ml of methanol. After two hours stirring at room temperature, 50 ml of water are added. The mixture is extracted three times with dichloromethane, the organic phases are collectively washed with water and dried over sodium sulphate. The solvent is removed in vacuo and the remaining residue is purified by chromatography on silica gel (eluent: ethylacetate/methanol=10/1). 100 mg of the title compound of m.p. 105-106° C. are obtained.

Workup

  1. extractionThe mixture is extracted three times with dichloromethane
  2. washthe organic phases are collectively washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent is removed in vacuo
  5. customthe remaining residue is purified by chromatography on silica gel (eluent: ethylacetate/methanol=10/1)

Sources & evidence

ORD record
ord-d64e770a7c0b42aca6b74b8c5138b116
Source dataset
uspto-grants-2002_05
Patent number
US06384048B1

Reaction notes

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