m-Chloroperbenzoic acid → MK 767 metabolite M16

HRID 49531ノート

反応式

HRID 49531 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 9955002MK 767 metabolite M16収率 73.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-10da85583c394c50886760665dd32c38
出典データセット
uspto-grants-2004_03
特許番号
US06706763B1

反応ノート

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