Water → HCID 19386046, compound

HRID 248647Notes

Reaction equation

HRID 248647 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([CH:20]=C)=[CH:15][CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:23].[Na+].O1CCCC1.O>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH:20]([C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][CH2:19][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]2)=[CH:16][CH:15]=1)=[O:23]

Participants

7

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 19386081HCID 19386081, compoundHCID 23667635Sodium periodate

Product 1

HCID 19386046HCID 19386046, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

A 2.5% solution of osmium tetroxide in tertbutanol (2 ml) is added to a mixture of the compound obtained in step b) above (1.4 g, 0.0049 mol), sodium periodate (3.5 g), tetrahydrofuran (40 ml), and water (10 ml). The reaction mixture is stirred at room temperature under nitrogen atmosphere for 1 hour, poured into water and extracted with ethyl acetate. The organic solution is washed with water, dried over sodium sulfate and concentrated under vacuum. The dark oily product which is thus obtained is purified by chromatography eluting with a mixture cyclohexane:ethyl acetate 6:4.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe dark oily product which is thus obtained
  6. customis purified by chromatography
  7. washeluting with a mixture cyclohexane:ethyl acetate 6:4

Sources & evidence

ORD record
ord-5365116336d640008ea76f8f5c7092d8
Source dataset
uspto-grants-1993_05
Patent number
US05210276

Reaction notes

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