(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 1934370노트

반응식

HRID 1934370 반응식
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]

참가 물질

5

반응물 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

생성물 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]naphthyridine수율 48%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d64e770a7c0b42aca6b74b8c5138b116
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384048B1

반응 노트

불러오는 중…