m-Chloroperbenzoic acid → HCID 20786193, compound

HRID 736500Notes

Reaction equation

HRID 736500 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:23][O:34]2)=[CH:18][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid3×HCID 516892Sodium BicarbonateHCID 20786194HCID 20786194, compound

Product 1

HCID 20786193HCID 20786193, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 291 (4.1 g, 12.1 mmol) in dry CHCl3 (60 mL) was added m-CPBA 70% (3.6 g, 14.5 mmol). The reaction mixture was stirred at room temperature for 5 h then additional m-CPBA (0.6 g, 2.4 mmol) was added and the stirring continued for 1 h. A further amount of m-CPBA (0.6 g, 2.4 mmol) was added and the reaction mixture was stirred for 16 h. Chloroform and a 10% solution of NaHCO3 were added and the phases were separated. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 1/3) to afford the title compound 292 (2.86 g, 8.07 mmol, 66% yield). 1H NMR (300 MHz, CDCl3) δ (ppm): 9.20 (s, 1H), 7.95 (d,J=8.1 Hz, 2H), 7.86-7.75 (m, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.26-7.10 (m, 3H), 6.84-6.70 (m, 1H), 3.93 (t, J=3.0 Hz, 1H), 3.20 (t, J=5.0 Hz, 1H), 2.80 (dd, J=5.0, 3.0 Hz, 1H), 1.52 (s, 9H).

Workup

  1. waitthe stirring continued for 1 h
  2. stirringthe reaction mixture was stirred for 16 h
  3. customthe phases were separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 1/3)

Sources & evidence

ORD record
ord-af551d60168d4bf0b973cb412a1beca3
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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