Water → HCID 57385684, compound

HRID 2406854Notes

Reaction equation

HRID 2406854 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[CH3:18])=[CH:6]/[C@@H:7]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@@H:12]2[C@@H:8]1[C@@H:9]([OH:17])[CH2:10][CH2:11]2)[CH3:2].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[CH3:18])=[CH:6]/[C@@H:7]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@@H:12]2[C@@H:8]1[C:9](=[O:17])[CH2:10][CH2:11]2)[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 25241888HCID 25241888, compound

Product 1

HCID 57385684HCID 57385684, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Compound (11a) is dissolved in an appropriate solvent, preferably in dimethylsulfoxide, and treated with a solution of IBX, preferably in dimethylsulfoxide. After stirring for up to several hours, water is added and the white precipitate is removed by filtration. The precipitate is washed, preferably with dimethylsulfoxide/water and a small amount of AcOEt. The filtrate is extracted, preferably with dichloromethane for several times, the combined organic phases are dried (using e.g. Na2SO4) and concentrated, preferably in vacuo. Chromatography purification (using e.g. a polar solvent gradient) is employed to yield compound (12a). The reaction of compound (11a) (A) and IBX (B) is preferably carried out with equivalents, on a molar basis, of A:B in the ratio of about 1:2.

Workup

  1. customthe white precipitate is removed by filtration
  2. washThe precipitate is washed, preferably with dimethylsulfoxide/water
  3. extractionThe filtrate is extracted, preferably with dichloromethane for several times
  4. dry with materialthe combined organic phases are dried (using e.g. Na2SO4)
  5. concentrationconcentrated, preferably in vacuo
  6. customChromatography purification (

Sources & evidence

ORD record
ord-dd0f1937a6164ca792ace36cdc9655c7
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

Loading…