(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 1934370ノート

反応式

HRID 1934370 の反応式
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]

参加物

5

反応物 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

生成物 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]naphthyridine収率 48%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d64e770a7c0b42aca6b74b8c5138b116
出典データセット
uspto-grants-2002_05
特許番号
US06384048B1

反応ノート

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