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Water → 1-[6-(5-{2-cyclopentyl-1-[5-(methylsulfonyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882099
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HRID 1882099 반응식
[CH:1]1([CH2:6][CH:7]([C:16]2[NH:20][C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:30])[CH2:28][OH:29])=[CH:23][CH:22]=3)=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11](SC)=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCC[CH2:32]1.O.O[O:38][S:39]([O-:41])=O.[K+]>C(OCC)(=O)C.CO>[CH:1]1([CH2:6][CH:7]([C:16]2[NH:20][C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:30])[CH2:28][OH:29])=[CH:23][CH:22]=3)=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:39]([CH3:32])(=[O:41])=[O:38])=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593313131-[6-(5-{2-cyclopentyl-1-[5-(methylsulfanyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

생성물 1

HCID 593313041-[6-(5-{2-cyclopentyl-1-[5-(methylsulfonyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol수율 43%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-[6-(5-{2-cyclopentyl-1-[5-(methylsulfanyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol (124 mg), tetrahydrofuran (2 mL), water (2 mL) and methanol (2 mL) was added Oxone (registered trademark) (216 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (57.1 mg, yield 43%) 15 was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (99:1, volume ratio). MS: 456 (MH+).

후처리

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-50e4006e93a641d98d91c6f5dd872352
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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