Water → HCID 67191851, compound

HRID 546220Notes

Reaction equation

HRID 546220 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][C:8]1[CH:9]=[C:10]([C@@H:16]([CH2:20][C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]2)[C:17]([OH:19])=[O:18])[CH:11]=[CH:12][C:13]=1[S:14][CH3:15].[Mn]([O-])(=O)(=O)=[O:28].[K+].[OH2:33]>CO>[CH3:15][S:14]([C:13]1[CH:12]=[CH:11][C:10]([C@@H:16]([CH2:20][C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]2)[C:17]([OH:19])=[O:18])=[CH:9][C:8]=1[CH3:7])(=[O:28])=[O:33]

Participants

6

Reactant 4

HCID 962Water2×HCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 67189647HCID 67189647, compound

Product 1

HCID 67191851HCID 67191851, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In a flask was placed sodium periodate (725 mg, 3.38 mmol) and water (6 mL). To this solution was then added (R)-2-(3-methyl-4-methylsulfanyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionic acid (525 mg, 1.80 mmol) in methanol (11 mL). The reaction was then stirred at 25° C. for 1 h after which time there was a white precipitate. The reaction was then filtered through a plug of celite and the celite pad washed with chloroform. The filterate was concentrated in vacuo and then azeotroped with acetonitrile. The residue was then dissolved in methanol (20 mL) and added slowly to a solution of potassium permanganate (425 mg, 2.70 mmol) in water (5 mL) and stirred at 25° C. for 1 h. After this time the reaction turned dark brown and the solids were filtered off and washed with methanol. The filterate was concentrated in vacuo and the residue was dissolved in acetonitrile with a small amount of methanol and then concentrated with silica gel (2 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 20% methanol/ethyl acetate) to afford (R)-2-(4-methanesulfonyl-3-methyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionic acid (523 mg, 90%) as a white solid: [α]31589=−90.0° (c=0.15, methanol); ES-HRMS m/e calcd for C16H20O5S (M+H)+ 325.1104, observed 325.1104; 1H NMR (300 MHz, DMSO-d6) δ 1.48 (m, 1H, CH), 1.78-2.35 (m, 8H, 4×CH2), 2.63 (s, 3H, ArCH3), 3.20 (s, 3H, SO2CH3), 3.67 (t, J=7.6 Hz, 1H, ArCHCO), 7.42 (m, 2H, Ar), 7.85 (d, Jo=8.6 Hz, 1H, Ar), 12.64 (s, 1H, CO2H).

Workup

  1. customIn a flask was placed
  2. filtrationThe reaction was then filtered through a plug of celite
  3. washthe celite pad washed with chloroform
  4. concentrationThe filterate was concentrated in vacuo
  5. customazeotroped with acetonitrile
  6. dissolutionThe residue was then dissolved in methanol (20 mL)
  7. stirringstirred at 25° C. for 1 h
  8. filtrationthe solids were filtered off
  9. washwashed with methanol
  10. concentrationThe filterate was concentrated in vacuo
  11. dissolutionthe residue was dissolved in acetonitrile with a small amount of methanol
  12. concentrationconcentrated with silica gel (2 g) in vacuo
  13. custompurified on Biotage Flash chromatography system (40M column, silica gel, 20% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-65b706ca43d64147a8d26762c656a51c
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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