m-Chloroperbenzoic acid → HCID 67733447, compound

HRID 1901638Notes

Reaction equation

HRID 1901638 reaction equation
[NH2:1][C@@H:2]([CH2:15][S:16][CH3:17])[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:15][S:16]([CH3:17])=[O:26])[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 67733455HCID 67733455, compound

Product 1

HCID 67733447HCID 67733447, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.54 g of (R)-3-(2-amino-3-methylthiopropoxy)-5-chloro-1,2-benzoisoxazole in 5 ml of methylene chloride is added 0.43 g of m-chloroperbenzoic acid with ice-cooling, and they are subjected to reaction at the same temperature for 30 minutes, after which 0.21 g of m-chloroperbenzoic acid is added and they are subjected to reaction for a further 30 minutes at the same temperature. After completion of the reaction, a saturated aqueous sodium hydrogencarbonate solution is added and shaken, after which the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:chloroform:methanol=20:1], to obtain 0.14 g of oily (R)-3-(2-amino-3-methanesulfinylpropoxy)-5-chloro-1,2-benzoisoxazole (Compound No. 139-1) and 0.38 g of oily (R)-3-(2-amino-3-methanesulfonylpropoxy)-5-chloro-1,2-benzoisoxazole (Compound No. 139-2).

Workup

  1. temperaturecooling
  2. customthey are subjected to reaction at the same temperature for 30 minutes
  3. customthey are subjected to reaction for a further 30 minutes at the same temperature
  4. customAfter completion of the reaction
  5. customafter which the organic layer is separated
  6. washThe separated organic layer is washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent is removed by distillation under reduced pressure
  9. customThe residue obtained
  10. customis purified by a column chromatography [eluant:chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-3aede325780d46829936b49d0fe9f421
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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