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 1407643노트

반응식

HRID 1407643 반응식
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

참가 물질

5

반응물 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

생성물 1

HCID 593523112,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,8'-[1,3]thiazolo[5,4-e]indol]-7'(6'H)-one수율 46.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

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).

후처리

  1. concentrationconcentrated in vacuo Water
  2. additionwas 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

출처 및 근거

ORD 기록
ord-6ee3456533df47e4b1cc57fab3e06663
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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