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Sulfuric Acid → HCID 69672878, 화합물

HRID 2406409
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HRID 2406409 반응식
C(O[C:5]([CH3:8])([CH3:7])[CH3:6])(=O)C.[CH2:9]([O:11][C:12](=[O:36])[CH:13]([OH:35])[C:14]1[C:15]([CH3:34])=[N:16][C:17]2[S:18][C:19]3[CH2:20][O:21][CH2:22][CH2:23][C:24]=3[C:25]=2[C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)[CH3:10].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:9]([O:11][C:12](=[O:36])[CH:13]([O:35][C:5]([CH3:8])([CH3:7])[CH3:6])[C:14]1[C:15]([CH3:34])=[N:16][C:17]2[S:18][C:19]3[CH2:20][O:21][CH2:22][CH2:23][C:24]=3[C:25]=2[C:26]=1[C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1)[CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

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반응물 4

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 516892Sodium BicarbonateHCID 69672802hydroxy-(2-methyl-4-p-tolyl-5,8-dihydro-6H-7-oxa-9-thia-1-aza-fluoren-3-yl)-acetic acid ethyl ester

생성물 1

HCID 69672878HCID 69672878, 화합물수율 45%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Tert-Butyl acetate (0.8 mL) was added to a solution of hydroxy-(2-methyl-4-p-tolyl-5,8-dihydro-6H-7-oxa-9-thia-1-aza-fluoren-3-yl)-acetic acid ethyl ester (100 mg, 0.252 mmol) in dichloromethane (0.8 mL) followed by concentrated sulphuric acid (40 μL) and the reaction stirred at room temperature for 2 hours. Sodium bicarbonate solution (10% aqueous, 2 mL) was added and the reaction evaporated in vacuo until only the aqueous remained. The aqueous was extracted with ethyl acetate (2 mL) and the organic layer washed with brine (1 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography on silica eluting with 0-30% ethyl acetate/heptanes to afford a colourless solid (66 mg, 45%). LCMS (12 min acidic) 7.25 min, ES+/AP+ 454 (MH+)

후처리

  1. customthe reaction evaporated in vacuo until only the
  2. extractionThe aqueous was extracted with ethyl acetate (2 mL)
  3. washthe organic layer washed with brine (1 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica eluting with 0-30% ethyl acetate/heptanes

출처 및 근거

ORD 기록
ord-6a3a3d66da0844e7846111eb7d5b8910
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809363B2

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