m-Chloroperbenzoic acid → MK 767 metabolite M16

HRID 49531노트

반응식

HRID 49531 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 9955002MK 767 metabolite M16수율 73.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-10da85583c394c50886760665dd32c38
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706763B1

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