Isopropanol → HCID 86753838, compound

HRID 1417630Notes

Reaction equation

HRID 1417630 reaction equation
[C:1]([O:4][C@@H:5]1[C:34]([CH3:36])([CH3:35])[C@H:33]2[C@@:8]3([O:29][C:12]4[C:13]5[CH2:14][NH:15][C:16](=[O:28])[C:17]=5[CH:18]=[C:19]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:11]=4[CH2:10][C@:9]3([CH3:38])[C@@H:30]([CH3:37])[CH2:31][CH2:32]2)[CH2:7][C@@H:6]1[OH:39])(=[O:3])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.C(=O)([O-])O.[Na+]>CC(C)=O>[C:1]([O:4][C@H:5]1[C:34]([CH3:36])([CH3:35])[C@H:33]2[C@@:8]3([O:29][C:12]4[C:13]5[CH2:14][NH:15][C:16](=[O:28])[C:17]=5[CH:18]=[C:19]([O:20][CH2:21][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:11]=4[CH2:10][C@:9]3([CH3:38])[C@@H:30]([CH3:37])[CH2:31][CH2:32]2)[CH2:7][C:6]1=[O:39])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 86753833HCID 86753833, compoundHCID 131709961Jones' reagent

Product 1

HCID 86753838HCID 86753838, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of Compound (49f) (Step-2 in Example 55) (116 mg, 0.22 mmol) in 5.0 ml of acetone was added dropwise 65 μl (0.26 mmol) of the Jones reagent under ice-cooling, and the mixture stirred for 30 min at the same temperature. To the reaction mixture was added 100 μl of isopropanol. The mixture was stirred for 5 min, neutralized with an aqueous saturated sodium hydrogen carbonate solution, and concentrated under reduced pressure to a half volume. After addition of water, the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (Merck, Lobar column, size A; toluene:ethyl acetate=1:1) to give 101 mg (87%) of Compound (52).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 5 min
  3. concentrationconcentrated under reduced pressure to a half volume
  4. additionAfter addition of water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by a column chromatography (Merck, Lobar column, size A

Sources & evidence

ORD record
ord-c189787928b64d9cb2598dae04858a15
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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