Water → 5-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

HRID 1841862노트

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HRID 1841862 반응식
[I-].[CH2:2]([C:4]1([O:9][C:10](=[O:36])[CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:34][CH3:35])=[C:19]([S+:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[C:23]4[CH:30]=[CH:31][CH:32]=[CH:33][C:22]3=4)[CH:20]=2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3].[F:37][C:38]([F:50])([S:46]([O-:49])(=[O:48])=[O:47])[CH2:39][O:40][C:41](=[O:45])[C:42]([CH3:44])=[CH2:43].C([NH+](CC)CC)C.O>ClCCl>[F:50][C:38]([F:37])([S:46]([O-:49])(=[O:48])=[O:47])[CH2:39][O:40][C:41](=[O:45])[C:42]([CH3:44])=[CH2:43].[CH2:2]([C:4]1([O:9][C:10](=[O:36])[CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:34][CH3:35])=[C:19]([S+:21]3[C:22]4[CH:33]=[CH:32][CH:31]=[CH:30][C:23]=4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=4)[CH:20]=2)=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8]1)[CH3:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 867124705-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium iodide

생성물 1

HCID 867124685-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate수율 86.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium iodide (10.0 g, 16.2 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (5.64 g, 17.0 mmol, 1.05 eq) were dissolved in dichloromethane (200 mL) and water (200 mL) and stirred at r.t. overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×250 mL). The combined organic layers were washed with water (3×250 mL), concentrated in vacuo and azeotroped with acetonitrile (2×100 mL) to afford the title compound (10.1 g, 86%) as a white hydroscopic solid. 1H NMR (300 MHz, (d-DMSO) δ: 8.52 (d, J=7.8 Hz, 2H), 8.35 (d, J=7.8 Hz, 2H), 8.27 (dd, J=8.1, 2.1 Hz, 1H), 7.98 (t, J=7.8 Hz, 2H), 7.78 (t, J=7.8 Hz, 2H), 7.55 (d, J=2.1 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 6.09-6.13 (m, 1H), 5.76-5.79 (m, 1H), 4.74 (s, 2H), 4.62 (dd, J=15.6, 15.6 Hz, 2H), 4.05 (s, 3H), 1.83-1.98 (m, 7H), 1.45-1.65 (m, 6H), 0.79 (t, J=6.6 Hz, 3H).

후처리

  1. customThe dichloromethane layer was separated
  2. washthe aqueous phase washed with dichloromethane (3×250 mL)
  3. washThe combined organic layers were washed with water (3×250 mL)
  4. concentrationconcentrated in vacuo
  5. customazeotroped with acetonitrile (2×100 mL)

출처 및 근거

ORD 기록
ord-962c0c0181b04624ab65d666f65abb2e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08945814B2

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