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Water → 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate

HRID 1841866
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HRID 1841866 반응식
[Br-].[CH3:2][C:3]1[CH:4]=[C:5]([S+:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]2=3)[CH:6]=[C:7]([CH3:23])[C:8]=1[O:9][CH2:10][C:11](=[O:22])[O:12][C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14].[CH3:37][C@:38]12[CH2:54][CH2:53][C:52](=[O:55])[CH2:51][CH:50]1[CH2:49][C:48](=[O:56])[C@@H:47]1[C@@H:39]2[CH2:40][C:41](=[O:77])[C@@:42]2([CH3:76])[C@H:46]1[CH2:45][CH2:44][C@@H:43]2[C@H:57]([CH3:75])[CH2:58][CH2:59][C:60]([O:62][CH2:63][CH2:64][C:65]([F:74])([F:73])[C:66]([F:72])([F:71])[S:67]([O-:70])(=[O:69])=[O:68])=[O:61].[Na+].O>ClCCl>[CH3:37][C@:38]12[CH2:54][CH2:53][C:52](=[O:55])[CH2:51][CH:50]1[CH2:49][C:48](=[O:56])[C@@H:47]1[C@@H:39]2[CH2:40][C:41](=[O:77])[C@@:42]2([CH3:76])[C@H:46]1[CH2:45][CH2:44][C@@H:43]2[C@H:57]([CH3:75])[CH2:58][CH2:59][C:60]([O:62][CH2:63][CH2:64][C:65]([F:74])([F:73])[C:66]([F:71])([F:72])[S:67]([O-:70])(=[O:68])=[O:69])=[O:61].[CH3:23][C:7]1[CH:6]=[C:5]([S+:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]2=3)[CH:4]=[C:3]([CH3:2])[C:8]=1[O:9][CH2:10][C:11](=[O:22])[O:12][C:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:15])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 58463086sodium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonateHCID 867124715-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide

생성물 1

HCID 86712475
5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate
수율 79.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide (1.8 g, 3.21 mmol) and sodium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate (2.13 g, 3.37 mmol) were dissolved in dichloromethane (50 mL) and water (50 mL) and stirred at room temperature overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×50 mL). The combined organic layers were washed with water (4×100 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×100 mL) to afford the title compound (2.77 g, 79%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.53 (d, J=8 Hz, 2H), 8.35 (d, J=8 Hz, 2H), 8.04 (t, J=7.5 Hz, 2H), 7.83 (t, J=7.5 Hz, 2H), 7.50 (s, 2H), 7.40 (d, J=8 Hz, 2H), 7.31 (t, J=8 Hz, 2H), 7.24 (t, J=8 Hz, 1H), 4.65 (s, 2H), 4.32 (t, J=6.5 Hz, 2H), 3.05-3.17 (m, 2H), 2.94 (t, J=12.5 Hz, 1H), 2.64-2.82 (m, 5H), 2.21-2.53 (m, 12H), 1.72-2.10 (m, 17H), 1.56-1.65 (m, 1H), 1.47 (s, 3H), 1.28-1.38 (m, 5H), 1.10 (s, 3H), 0.83-0.87 (m, 3H).

후처리

  1. customThe dichloromethane layer was separated
  2. washthe aqueous phase washed with dichloromethane (3×50 mL)
  3. washThe combined organic layers were washed with water (4×100 mL)
  4. concentrationconcentrated in vacuo and residual water
  5. customremoved via azeotrope with acetonitrile (2×100 mL)

출처 및 근거

ORD 기록
ord-0d75c229b23d4d62ab1959b7b0c74c70
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08945814B2

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