m-Chloroperbenzoic acid → MK 767 metabolite M20

HRID 49532Notes

Reaction equation

HRID 49532 reaction equation
[C:1]([CH:4]([S:28]([CH3:30])=[O:29])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:26][CH3:27])=[C:10]([CH:25]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[O:12])(=[O:3])[NH2:2].C1C=C(Cl)C=C(C(OO)=[O:39])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([CH:4]([S:28]([CH3:30])(=[O:39])=[O:29])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:26][CH3:27])=[C:10]([CH:25]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=1)=[O:12])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 9955002MK 767 metabolite M16

Product 1

HCID 9890351MK 767 metabolite M20Yield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 274 mg of 5-[2-carbamoyl-2-(methylsulfinyl)ethyl]-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 100 ml of methylene chloride and 155 mg of mCPBA, and the mixture was stirred for 3 hours. Saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, and the insolubles were filtered off. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel, methylene chloride:methanol=50:1 to 20:1) to obtain 201 mg of aimed product as colorless crystals.

Workup

  1. filtrationthe insolubles were filtered off
  2. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSolvent was distilled off under reduced pressure
  5. customthe residue obtained
  6. customwas purified by means of column chromatography (silica gel, methylene chloride:methanol=50:1 to 20:1)

Sources & evidence

ORD record
ord-0fabe480a1834f719d2adcc258684f2b
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Reaction notes

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