Trifluoromethanesulfonic acid → 2,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,8'-[1,3]thiazolo[5,4-e]indol]-7'(6'H)-one

HRID 2385220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2385220
COC1C=CC(C[N:8]2[C:16]3[C:11](=[C:12]4[S:19][CH:18]=[N:17][C:13]4=[CH:14][CH:15]=3)[C:10]3([C:31]4[C:22](=[CH:23][C:24]5[O:29][CH2:28][CH2:27][O:26][C:25]=5[CH:30]=4)[O:21][CH2:20]3)[C:9]2=[O:32])=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl.FC(F)(F)C(O)=O>[S:19]1[C:12]2=[C:11]3[C:16](=[CH:15][CH:14]=[C:13]2[N:17]=[CH:18]1)[NH:8][C:9](=[O:32])[C:10]13[C:31]2[C:22](=[CH:23][C:24]3[O:29][CH2:28][CH2:27][O:26][C:25]=3[CH:30]=2)[O:21][CH2:20]1

Komponenten

5

Edukt 2

HCID 62406Trifluoromethanesulfonic acidHCID 593523706'-(4-methoxybenzyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,8'-[1,3]thiazolo[5,4-e]indol]-7'(6'H)-one

Produkt 1

HCID 593523112,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,8'-[1,3]thiazolo[5,4-e]indol]-7'(6'H)-oneAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a solution of 6′-(4-methoxybenzyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,8′-[1,3]thiazolo[5,4-e]indol]-7′(6′H)-one (1.9 g, 4.0 mmol) in dichloromethane (40 mL) and trifluoroacetic acid (40 mL) was added at ambient temperature trifluoromethanesulfonic acid (1.8 mL, 20 mmol). The mixture was stirred at ambient temperature for 16 h and concentrated in vacuo. Water was added to the residue and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate and water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography and eluted with 50% ethyl acetate in hexanes to afford 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,8′-[1,3]thiazolo[5,4-e]indol]-7′(6′H)-one (0.65 g, 44%): 1H NMR (300 MHz, CDCl3) δ10.86 (s, 1H), 9.06 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.14 (d, J=8.5 Hz, 1H), 6.54 (s, 1H), 6.21 (s, 1H), 4.68 (s, 2H), 4.19-4.01 (m, 4H); MS (ES+) m/z 353.1 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c9b6feb6d33249efa9ce4609b89d3575
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263606B2

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