m-Chloroperbenzoic acid → HCID 59792353, compound

HRID 1645563Notes

Reaction equation

HRID 1645563 reaction equation
[CH2:1]1[C:4]2([O:9][CH2:8][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([CH2:19][S:20][C:21]4[NH:25][C:24]5[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=5[N:22]=4)[C:13]=3[CH3:30])[CH2:6][O:5]2)[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:39])C=1.C(=O)([O-])O.[Na+]>CO.C1(C)C=CC=CC=1>[CH2:3]1[C:4]2([O:5][CH2:6][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([CH2:19][S:20]([C:21]4[NH:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)=[O:39])[C:13]=3[CH3:30])[CH2:8][O:9]2)[CH2:1][CH2:2]1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59792604HCID 59792604, compound

Product 1

HCID 59792353HCID 59792353, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent2×

Procedure

To a toluene (20 ml)-methanol (2 ml) solution of the 2-(((4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzimidazole (499 mg, 1.17 mmol) obtained in the step (13d), a toluene (1 ml)-methanol (1 ml) solution of 3-chloroperbenzoic acid (280 mg, 1.05 mmol as the content was regarded as 65%) was added dropwise at −65° C. for 5 minutes in a nitrogen atmosphere. The mixture was stirred in the same conditions for 55 minutes. To the reaction mixture, a saturated aqueous solution of sodium hydrogen carbonate was added. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (NH silica gel: 20 g, elution solvent: dichloromethane, dichloromethane/methanol=20/1). The fractions containing the title compound were collected with ethyl acetate, and concentrated. To the residue, diethyl ether was added and then the mixture was concentrated to obtain the title compound (445 mg, yield: 86.1%) as a colorless foam.

Workup

  1. additionwas added dropwise at −65° C. for 5 minutes in a nitrogen atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (NH silica gel: 20 g, elution solvent: dichloromethane, dichloromethane/methanol=20/1)
  7. additionThe fractions containing the title compound
  8. customwere collected with ethyl acetate
  9. concentrationconcentrated
  10. additionTo the residue, diethyl ether was added
  11. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-85c52ace02e945f685909bbe54c13457
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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