m-Chloroperbenzoic acid → HCID 10319431, compound

HRID 618759Notes

Reaction equation

HRID 618759 reaction equation
[C:1]1([S:7]([NH:10][CH2:11][CH2:12][S:13][C:14]2[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[C:1]1([S:7]([NH:10][CH2:11][CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=2)=[O:35])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9978005HCID 9978005, compound

Product 1

HCID 10319431HCID 10319431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 4-[2-(phenylsulfonylamino)ethylthio]phenoxyacetate (2 g) obtained in Example 3 in methylene chloride (30 ml) was added dropwise under ice cooling a solution of m-chloroperbenzoic acid (0.87 g) in methylene chloride (20 ml). The reaction mixture was stirred at room temperature for an hour, washed with an aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue, which was then chromatographed on silica gel column (eluent; ethyl acetate) and recrystallized from ethyl acetate to give ethyl 4-[2-(phenylsulfonylamino)ethylsulfinyl]phenoxyacetate (Compound No. 38) (1.76 g).

Workup

  1. washwashed with an aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a residue, which
  5. customwas then chromatographed on silica gel column (eluent; ethyl acetate)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a3668a3631f540228687bb2435943da3
Source dataset
uspto-grants-1999_09
Patent number
US05955505

Reaction notes

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