m-Chloroperbenzoic acid → HCID 57697651, compound

HRID 1674517Notes

Reaction equation

HRID 1674517 reaction equation
[NH:1]([C:8]([N:10]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=3)=[N:22][CH:23]=2)[CH2:13][CH2:12]1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:50])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[NH:1]([C:8]([N:10]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:11]1[CH2:12][CH2:13][N+:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])=[CH:27][CH:26]=3)=[N:22][CH:23]=2)([O-:50])[CH2:15][CH2:16]1)=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66814655HCID 66814655, compound

Product 1

HCID 57697651HCID 57697651, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound prepared in Example 8(10) (361 mg) in chloroform (6.1 ml) was added m-chloroperbenzoic acid (116 mg) on ice bath. The reaction mixture was stirred for 4 hours at room temperature. To reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was washed with chloroform and methanol, dried to give the compound of the present invention (194 mg) having the following physical data.

Workup

  1. customTo reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washThe obtained residue was washed with chloroform and methanol
  7. customdried
  8. customto give the compound of the present invention (194 mg)

Sources & evidence

ORD record
ord-79bc77a3e05a4aa481bacd851e0fa735
Source dataset
uspto-grants-2011_08
Patent number
US08003642B2

Reaction notes

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