m-Chloroperbenzoic acid → HCID 19800988, compound

HRID 1646641Notes

Reaction equation

HRID 1646641 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:16][S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:15])[CH:11]([C:24]2([CH3:32])[O:31][CH:25]2[CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[CH:10]1[O:33][CH3:34])=[O:7])=[O:4].ClC1C=CC=C(C(OO)=[O:43])C=1>ClCCl.C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:16][S:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:43])([OH:15])[CH:11]([C:24]2([CH3:32])[O:31][CH:25]2[CH2:26][CH:27]=[C:28]([CH3:29])[CH3:30])[CH:10]1[O:33][CH3:34])=[O:7])=[O:4]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86746494HCID 86746494, compound

Product 1

HCID 19800988HCID 19800988, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In dichloromethane (2 ml) was dissolved 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-h-exenyl)-3-methoxy-1-phenylthiomethyl-1,4-cyclohexanediol (200 mg). To the solution was added, under ice-cooling, m-chloroperbenzoic acid (80.9 mg), and the mixture was stirred for 30 minutes. The reaction mixture was diluted with ethyl acetate (70 ml), which was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was then purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: ethyl acetate - hexane=1:2) to afford 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-phenylsulfinylmethyl-1,4-cyclohexanediol (175 mg: yield 85%) as colorless powder.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. washwas washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was then purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: ethyl acetate - hexane=1:2)

Sources & evidence

ORD record
ord-35000a97a6414dce9b97284232e8a16a
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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