m-Chloroperbenzoic acid → HCID 66594458, compound

HRID 1093503Notes

Reaction equation

HRID 1093503 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=3)=[C:20]([C:36]([F:39])([F:38])[F:37])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.[Cl:41]C1C=CC=C(C(OO)=[O:49])C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[ClH:41].[NH2:7][C:8]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:35])=[O:49])=[CH:30][CH:29]=2)=[C:20]([C:36]([F:39])([F:38])[F:37])[CH:19]=1)([CH2:13][OH:12])[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 59407967HCID 59407967, compound

Product 1

HCID 66594458HCID 66594458, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 96-3 (720 mg) was dissolved in methylene chloride (20 ml), m-chloroperbenzoic acid (containing 25% water, 293 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 20 hr. m-Chloroperbenzoic acid (containing 25% water, 234 mg) was further added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethanol (15 ml), concentrated hydrochloric acid (1.5 ml) was added, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give a white powder. The white powder was separated by HPLC using capcellpac (registered trade mark) UG80 (0.05% trifluoroacetic acid-water/0.05% trifluoroacetic acid-acetonitrile), and the residue obtained by collecting a peak with a shorter retention time (primary peak) was converted to hydrochloride by the addition of hydrogen chloride containing ether (1 mol/l, 10 ml), and the precipitate was collected by filtration and dried to give the object product (75 mg) as a white powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. extractionthe mixture was extracted with chloroform
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in ethanol (15 ml)
  9. additionconcentrated hydrochloric acid (1.5 ml) was added
  10. stirringthe mixture was stirred at 80° C. for 1 hr
  11. concentrationThe reaction mixture was concentrated
  12. washthe residue was washed with diethyl ether
  13. customto give a white powder
  14. customThe white powder was separated by HPLC
  15. customthe residue obtained
  16. customby collecting a peak with a shorter retention time (primary peak)
  17. additionwas converted to hydrochloride by the addition of hydrogen chloride
  18. additioncontaining ether (1 mol/l, 10 ml)
  19. filtrationthe precipitate was collected by filtration
  20. customdried

Sources & evidence

ORD record
ord-39f9bca17933467a8a899388c4434da8
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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