Sodium periodate → HCID 178495704, compound

HRID 1900067Notes

Reaction equation

HRID 1900067 reaction equation
[CH3:1][O:2][CH2:3][C@@H: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][C@H: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 178495703HCID 178495703, compound

Product 1

HCID 178495704HCID 178495704, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

10.7 g (29.28 mmol) of (R)-5-methoxymethyl-3-[4-(trans-4-methylsulfanylmethoxy-cyclohexyl)-phenyl]-oxazolidin-2-one were dissolved in 500 ml of methanol, cooled to 0° and treated dropwise while stirring during 90 minutes with a solution of 4.7 g (22.0 mmol) of sodium periodate in 150 ml of water. The reaction mixture was stirred in a cold storage chamber at 4°-5° for 19 hours. Thereafter, it was diluted with 1 l of water and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and filtered. The filtrate was filtered through a 400 g silica gel 60 pad and washed in succession and separately with ethyl acetate (800 ml), methanol (1 l) and tetrahydrofuran (800 ml). 3.16 g of educt remained behind after evaporation of the ethyl acetate eluate. After evaporation the methanol and tetrahydrofuran eluates gave 8.11 g of (R)-3-[4-(trans-4-methanesulfinylmethoxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one (S-oxide R:S=1:1 diastereomer mixture) as a yellow oil, b.p. 205°/0.02 mbar, [α]D =-32.2° (c=1.0%, DMSO).

Workup

  1. temperaturecooled to 0°
  2. additiontreated dropwise
  3. extractionextracted 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 a 400 g silica gel 60 pad
  8. washwashed in succession and separately with ethyl acetate (800 ml), methanol (1 l) and tetrahydrofuran (800 ml)
  9. customafter evaporation of the ethyl acetate eluate
  10. customAfter evaporation the methanol and tetrahydrofuran eluates

Sources & evidence

ORD record
ord-66b62715b99e4e6bb1b06d2c9c1d679f
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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