Potassium Carbonate → HCID 86584563, Verbindung

HRID 1061285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061285
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH2:17](OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O)[CH:18]1[O:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:14][C:12]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][CH2:17][CH:18]3[CH2:19][O:20]3)[CH:3]=2)[NH:7][C:6]=1[CH3:11])=[O:13])[CH3:16]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 820731H-Indole-3-carboxylic acid, 5-hydroxy-2-methyl-, ethyl esterHCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonate

Produkt 1

HCID 86584563HCID 86584563, VerbindungAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 2.19 g (10 mmol) of ethyl 5-hydroxy-2-methyl-indole-3-carboxylate, 2.6 g (10 mmol) of 2S(+) glycidyl-3-nitrobenzenesulfonate and 1.5 g (11 mmol) of potassium carbonate in 25 mL reagent grade acetone was refluxed overnight. The mixture was then allowed to cool to room temperature and the solids were removed by vacuum filtration. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organics were washed once with water, twice with brine, dried over sodium sulfate and concentrated in vacuo. Then the solid was dried under vacuum to give 2.65 g of the title compound as a dull tan solid; mp 93-94° C.; 1H NMR (300 MHz, CDCl3) δ 1.44 (t, J=5.3 Hz, 3H), 2.71 (s, 3H), 2.74-2.80 (m, 1H), 2.92 (t, J=4.7 Hz, 1H), 3.37-3.43 (m, 1H), 4.00-4.06 (m, 1H), 4.27-4.31 (m, 1H), 4.37 (q, J=5.3Hz, 2H), 6.86 (dd, J=5.5, 3.0Hz, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.67 (d, J=3.0 Hz, 1H), 8.32 (s, 1H); MS (ES) m/z: 275.9 (MH+); HRMS Calcd. for C15H18NO4 (MH+): 276.1236. Found: 276.1228.

Aufarbeitung

  1. customthe solids were removed by vacuum filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organics were washed once with water, twice with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThen the solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5f74d0d1ec5d44779391a11ba0fe8159
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525202B2

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