m-Chloroperbenzoic acid → 2-Acetamido-1,3-diacetoxy-2-(4-octylsulfonylbenzyl)propane

HRID 862862Notes

Reaction equation

HRID 862862 reaction equation
[C:1]([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])=[CH:19][CH:18]=1)([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:6][O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:41])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:41])=[O:24])=[CH:19][CH:18]=1)([CH2:6][O:7][C:8](=[O:10])[CH3:9])[CH2:11][O:12][C:13](=[O:15])[CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 218492772-Acetamido-1,3-diacetoxy-2-(4-octylsulfinylbenzyl)propane

Product 1

HCID 218493422-Acetamido-1,3-diacetoxy-2-(4-octylsulfonylbenzyl)propaneYield 47.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution (10 ml) of 2-acetamido-1,3-diacetoxy-2-(4-octylsulfinylbenzyl)propane (330 mg) in chloroform was added m-chloroperbenzoic acid (244 mg) under ice-cooling. The mixture was stirred for 2.5 hours and then at room temperature for 1.5 hours. Calcium hydroxide (0.1 g) was added to the reaction mixture and the mixture was stirred at room temperature for 45 minutes. The insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give 162 mg of the subject compound.

Workup

  1. temperaturecooling
  2. waitat room temperature for 1.5 hours
  3. stirringthe mixture was stirred at room temperature for 45 minutes
  4. filtrationThe insoluble matters were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5505b5e667d847a0be6fa845705d47a2
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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