m-Chloroperbenzoic acid → MK 767 metabolite M16

HRID 49531Notes

Reaction equation

HRID 49531 reaction equation
[C:1]([CH:4]([S:28][CH3:29])[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:38])C=1>C(Cl)Cl>[C:1]([CH:4]([S:28]([CH3:29])=[O:38])[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:22])([F:24])[F:23])=[CH:17][CH:16]=1)=[O:12])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 99103294-Methoxy-alpha-(methylthio)-3-((((4-(trifluoromethyl)phenyl)methyl)amino)carbonyl)benzenepropanamide

Product 1

HCID 9955002MK 767 metabolite M16Yield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 639 mg of 5-[2-carbamoyl-2-(methylthio)ethyl]-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 70 ml of methylene chloride and 368 mg of mCPBA under cooling with ice, and the mixture was stirred for 3 hours. The reaction mixture 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 486 mg of aimed product as colorless crystals.

Workup

  1. temperatureunder cooling with ice
  2. washThe reaction mixture 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-10da85583c394c50886760665dd32c38
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Reaction notes

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