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m-Chloroperbenzoic acid → 6-bromo-2-(4-methanesulfinylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750294
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HRID 750294 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].ClC1C=CC=C(C(OO)=[O:40])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:31])=[O:40])=[CH:28][CH:29]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]
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참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 69155526HCID 69155526, 화합물

생성물 1

HCID 691569256-bromo-2-(4-methanesulfinylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester수율 46.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution (6.7 ml) of 6-bromo-2-(4-methylsulfanylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (334 mg) in dichloromethane was added m-chloro perbenzoic acid (200 mg) at 0° C. with stirring, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was washed with 1N sodium hydroxide and water, and the organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-1/4) to give the title compound (160 mg) as colorless crystals.

후처리

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. washThe reaction mixture was washed with 1N sodium hydroxide and water
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-1/4)

출처 및 근거

ORD 기록
ord-c84881d50c584d0cbe93fa77394cf6c8
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07402595B2

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