(Trifluoromethyl)trimethylsilane → Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-(2,2,2-trifluoro-1-hydroxyethyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 17087

反応式

HRID 17087 の反応式
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]=[O:30])[CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[C:8](=[O:11])[O:9][CH3:10].C[Si](C)(C)[C:44]([F:47])([F:46])[F:45].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]([F:40])([F:41])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:35]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([OH:30])[C:44]([F:47])([F:46])[F:45])[CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[C:8](=[O:11])[O:9][CH3:10]

参加物

5

反応物 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 11699919Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-formyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

生成物 1

HCID 11542018Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-(2,2,2-trifluoro-1-hydroxyethyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-formyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 73, 184 mg, 0.31 mmol) in anhydrous tetrahydrofuran at 0° C., 0.5 M trimethyl(trifluoromethyl) silane (2.5 mL, 1.24 mmol) and a catalytic amount of tetrabutylammonium fluoride were added. The reaction was stirred with gradual warming to room temperature. Once the reaction was complete, it was quenched with saturated ammonium chloride solution. The organic was extracted with methylene chloride, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by preparative thin layer chromatography using 1:4 acetone:hexane. 1H NMR (CDCl3, 600 MHz) δ 7.74 (s, 1H), 7.61 (m, 1H), 7.15-7.56 (m, 6H), 6.99 (m, 1H), 4.97 (m, 1H), 4.19-4.38 (m, 4H), 3.61-3.76 (m, 6H). LC-MS (M+Na) 686.9 (4.28 min).

後処理

  1. customit was quenched with saturated ammonium chloride solution
  2. extractionThe organic was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb3af6c442354febb736dcc3fe9555de
出典データセット
uspto-grants-2010_06
特許番号
US07737295B2

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