Sodium periodate → HCID 178494577, compound

HRID 1900068Notes

Reaction equation

HRID 1900068 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([O:22][CH2:23][S:24][CH3:25])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5]1.I([O-])(=O)(=O)=[O:27].[Na+]>CO.O>[CH3:25][S:24]([CH2:23][O:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:13]2[CH:12]=[CH:11][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1)=[O:27]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 178494576HCID 178494576, compound

Product 1

HCID 178494577HCID 178494577, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1.71 g (4.68 mmol) of (RS)-5-methoxymethyl-3-[4-(trans-4-methylsulfanylmethoxy-cyclohexyl)-phenyl]-oxazolidin-2-one were dissolved in 100 ml of methanol, cooled to 0° and treated dropwise while stirring during 40 minutes with a solution of 1.0 g (4.68 mmol) of sodium metaperiodate dissolved in 40 ml of water. The reaction mixture was held at about 4° for 24 hours. Thereafter, it was diluted with water and the product was extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and filtered. The filtrate was filtered through 50 g of silica gel 60 and washed separately with methanol. After evaporation of the methanol eluate the diastereomer mixture, (RS)-3-[4-(trans-4-methanesulfinylmethoxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one, was crystallized from benzene. M.p.: 98°-100°.

Workup

  1. temperaturecooled to 0°
  2. additiontreated dropwise
  3. extractionthe product was extracted with methylene chloride
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. filtrationThe filtrate was filtered through 50 g of silica gel 60
  8. washwashed separately with methanol
  9. customAfter evaporation of the methanol
  10. customwas crystallized from benzene

Sources & evidence

ORD record
ord-99bb05de9e784bda86665d5adb373b6b
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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