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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
ノート
印刷プレビュー

反応式

HRID 1841866 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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
収率 79.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0d75c229b23d4d62ab1959b7b0c74c70
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08945814B2

反応ノート

読み込み中…

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