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Sodium Thiosulfate → HCID 86703314, 화합물

HRID 2409997
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HRID 2409997 반응식
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH:2]([C:3]1[N:8]=[C:7]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:6]=[CH:5][CH:4]=1)=[O:1]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86703313HCID 86703313, 화합물

생성물 1

HCID 86703314HCID 86703314, 화합물수율 81.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-(6-hydroxymethylpyridin-2-ylmethyl)-6-methoxy-2-phenyl-1H-indole-1-carboxylate (600 mg) in dichloromethane (6 mL) was added Dess-Martin periodinane (744 mg), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L aqueous sodium thiosulfate solution, followed by stirring for 5 minutes. The mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (486 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 4.15 (2H, s), 6.84 (1H, dd, J=2.3, 8.7 Hz), 7.15-7.21 (1H, m), 7.28-7.44 (6H, m), 7.61-7.69 (1H, m), 7.72-7.77 (1H, m), 7.86 (1H, d, J=2.3 Hz), 10.02-10.05 (1H, m).

후처리

  1. stirringby stirring for 5 minutes
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-985f3498938e477a8908bb4f5d40da99
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815903B2

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