Acetone → HCID 67191351, compound

HRID 546175Notes

Reaction equation

HRID 546175 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:10]([CH2:14][CH:15]2[CH2:18][C:17](=[O:19])[CH2:16]2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1SC.[S:20]([O-:25])(O[O-])(=O)=[O:21].[K+].[K+].[Mn]([O-])(=O)(=O)=O.[K+].[CH3:34]C(C)=O>O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:10]([CH2:14][CH:15]2[CH2:16][C:17](=[O:19])[CH2:18]2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:20]([CH3:34])(=[O:25])=[O:21]

Participants

7

Reactant 4

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 10313463Potassium peroxymonosulphateHCID 671903062(R)-(3-chloro-4-methylsulfanyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid

Product 1

HCID 67191351HCID 67191351, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To the solution of 2(R)-(3-chloro-4-methylsulfanyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid (0.56 g, 1.88 mmol) dissolved in acetone (15 ml) and cooled to 0° C. in an ice bath was added potassium peroxymonosulfate (Oxone R, 2.3 g, 3.76 mmol) in water (6 ml). The ice bath was removed and the reaction stirred at 25° C. for 20 min. After such a time, it was filtered and washed with acetone and then concentrated in vacuo to remove acetone. The residue was dissolved in ethyl acetate, washed with water and then saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting reaction was dissolved in methanol and cooled to 0° C. in an ice bath. To this was slowly added potassium permanganate (0.32 g, 2.02 mmol) dissolved in water (8 ml). The reaction was then allowed to warm to 25° C. and stirred for 3 h. After this time it was filtered through short celite pad, washed with methanol and evaporated in vacuo. Purification on an AnaLogix Intelliflash system (40 g column, 3% methanol/methylene chloride+1% acetic acid) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid (0.13 g, 21%) as a white foam: 1H NMR (300 MHz, CDCl3) δ ppm 2.07-2.18 (m, 1H, CH of CH2), 2.26-2.50 (m, 2H, CH and CH of CH2), 2.64-2.85 (m, 2H, 2×CH or 2×CH2), 3.09-3.24 (m, 2H, 2×CH or 2×CH2), 3.28 (s, 3H, SO2CH3), 3.65 (t, J=7.4 Hz, 1H, ArCHCO2), 7.44 (dd, Jm=1.6 Hz, Jo=8.2 Hz, 1H, Ar), 7.55 (d, Jm=1.6 Hz, 1H, Ar), 8.15 (d, Jo=8.2 Hz, 1 H, Ar).

Workup

  1. customThe ice bath was removed
  2. filtrationAfter such a time, it was filtered
  3. washwashed with acetone
  4. concentrationconcentrated in vacuo
  5. customto remove acetone
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialsaturated aqueous sodium chloride solution, dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting reaction
  12. temperaturecooled to 0° C. in an ice bath
  13. temperatureto warm to 25° C.
  14. stirringstirred for 3 h
  15. filtrationAfter this time it was filtered through short celite pad
  16. washwashed with methanol
  17. customevaporated in vacuo
  18. customPurification on an AnaLogix Intelliflash system (40 g column, 3% methanol/methylene chloride+1% acetic acid)

Sources & evidence

ORD record
ord-4255e01eeb2e422288e3ecce99447d08
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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