Water → HCID 22449496, compound

HRID 964686Notes

Reaction equation

HRID 964686 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2].S([O-])([O-])(=O)=[O:17].[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].O>CC(C)=O>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[C:7](=[O:17])[CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 10488534HCID 10488534, compound

Product 1

HCID 22449496HCID 22449496, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a-solution of the compound obtained in (6) above (9.46 gm) in 420 ml of acetone was added 42 ml of 15% aqueous solution of magnesium sulfate. After cooling to 0° C., 21.7 gm of potassium permanganate was added to the mixture, a bit at a time. The mixture was stirred for 50 minutes at 0° C. and for 1 hour at room temperature. Upon addition of 1 l of water, the reaction product was extracted 3 times with chloroform. The chloroform layer was washed with water and saturated brine in this order, and dried over anhydrous-sodium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (3:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 7.98 gm of the title compound.

Workup

  1. extractionthe reaction product was extracted 3 times with chloroform
  2. washThe chloroform layer was washed with water and saturated brine in this order
  3. dry with materialdried over anhydrous-sodium sulfate
  4. customThe solvent was evaporated
  5. customto obtain fractions
  6. additioncontaining the target compound
  7. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-6190135b5d0f448d97874d46fa061b63
Source dataset
uspto-grants-1998_06
Patent number
US05770605

Reaction notes

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