Methanol--water (1/1) → 3-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 852665Notes

Reaction equation

HRID 852665 reaction equation
CS[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:11]=1)[C:6]([OH:8])=[O:7].O[O:19][S:20]([O-:22])=O.[K+].[CH3:24]O.O>>[CH3:24][S:20]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:22])=[O:19]

Participants

4

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 693576453-Methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid

Product 1

HCID 210741993-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acidYield 86%

Procedure

To a solution of 3-methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A1) (59 mg, 0.235 mmol, 1 equiv) in MeOH/H2O (3:1, 24 ml) was added oxone (578 mg, 0.94 mol, 4 equiv). The resulting mixture was stirred at room temperature for 50 min and then concentrated in vacuo. The residue was partitioned between AcOEt and H2O and the layers separated. The organic layer was washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo to give a solid which was triturated with Et2O to give 3-methanesulfonyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A5) (57 mg, 86%) as a white solid. [M+H]+=284.0, RT=2.05 min

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between AcOEt and H2O
  3. customthe layers separated
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a solid which
  8. customwas triturated with Et2O

Sources & evidence

ORD record
ord-f26ff93a345a4bea925d2c8bec78a1dc
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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