m-Chloroperbenzoic acid → methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfinyl)-propionate

HRID 49535ノート

反応式

HRID 49535 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([S:15][CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[C:17](=[O:30])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([S:15]([CH3:16])=[O:39])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[C:17](=[O:30])[NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 12094666HCID 12094666、化合物

生成物 1

HCID 12094667methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfinyl)-propionate収率 78.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1.50 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylthio)propionate in 30 ml of methylene chloride were added 800 mg of mCPBA under cooling with ice, and the mixture was stirred for 30 minutes. 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=100:1 to 50:1) to obtain 1.22 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfinyl)-propionate as colorless crystals. To a solution of 1.02 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]-carbamoylphenyl]-2-(methylsulfinyl)propionate obtained in 20 ml of methylene chloride were added 550 mg of mCPBA under cooling with ice, and the mixture was stirred for 7 hours at room temperature. 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 crystals obtained were recrystallized from hexane-ethyl acetate to obtain 750 mg of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfonyl)propionate as colorless crystals. Melting point 144-145° C.

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=100:1 to 50:1)

出典と根拠

ORDレコード
ord-70df0fea979a468b858395dd28e24c04
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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