Sodium periodate → (5R)-3-[6-(2-{[3-(Cyclopentylsulfinyl)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 503097노트

반응식

HRID 503097 반응식
I([O-])(=O)(=O)=[O:2].[Na+].[CH:7]1([S:12][C:13]2[CH:14]=[C:15]([CH:45]=[CH:46][CH:47]=2)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:31][C@@H:30]([C:32]3[CH:43]=[CH:42][C:35]4[O:36][C:37]([CH3:41])([CH3:40])[O:38][CH2:39][C:34]=4[CH:33]=3)[O:29][C:28]2=[O:44])[CH2:11][CH2:10][CH2:9][CH2:8]1>C(O)C.O>[CH:7]1([S:12]([C:13]2[CH:14]=[C:15]([CH:45]=[CH:46][CH:47]=2)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:31][C@@H:30]([C:32]3[CH:43]=[CH:42][C:35]4[O:36][C:37]([CH3:41])([CH3:40])[O:38][CH2:39][C:34]=4[CH:33]=3)[O:29][C:28]2=[O:44])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

5

반응물 2

HCID 23667635Sodium periodateHCID 66845210(5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

생성물 1

HCID 66845815(5R)-3-[6-(2-{[3-(Cyclopentylsulfinyl)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one수율 85.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Sodium periodate (333 mg) was added to a solution of (5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (230 mg) in ethanol (12 ml) and water (4 ml). The mixture was stirred at room temperature under nitrogen for 3 h. and the ethanol evaporated in vacuo. The aqueous phase was diluted with water and extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4) filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 10% to 100% ethyl acetate-cyclohexane, to give the title compound (201 mg). LCMS RT=3.54 min.

후처리

  1. customthe ethanol evaporated in vacuo
  2. additionThe aqueous phase was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with a stepped gradient of 10% to 100% ethyl acetate-cyclohexane

출처 및 근거

ORD 기록
ord-870480361273469a99934940a77ae398
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776895B2

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