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Diisopropylethylamine → Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 1055335
ノート
印刷プレビュー

反応式

HRID 1055335 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[C:23]([C:25]1[CH:26]=[C:27]([CH2:31][NH:32][C:33]([CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][CH:40]([O:43][C:44](=[O:58])[NH:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:39][CH2:38]2)=[O:34])[CH:28]=[CH:29][CH:30]=1)=[O:24].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:23]([C:25]2[CH:26]=[C:27]([CH2:31][NH:32][C:33]([CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][CH:40]([O:43][C:44](=[O:58])[NH:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=4[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[CH2:41][CH2:42]3)=[O:34])[CH:28]=[CH:29][CH:30]=2)=[O:24])=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 111266244-(1,3-Dioxolan-2-yl)anilineHCID 86646969Biphenyl-2-ylcarbamic acid 1-{2-[(3-chlorocarbonylphenyl)methylcarbamoyl]ethyl}piperidin-4-yl ester

生成物 1

HCID 66771841Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester
収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 4-(1,3-dioxolan-2-yl)phenylamine (0.0826 g, 0.500 mmol) and N,N-diisopropylethylamine (348 μL, 2.00 mmol) in DCM (2.0 mL) at room temperature was added a solution of biphenyl-2-ylcarbamic acid 1-{2-[(3-chlorocarbonylphenyl)methylcarbamoyl]ethyl}piperidin-4-yl ester (0.260 g, 0.500 mmol) in DCM (1.0 mL). The resulting mixture was stirred at room temperature for 1 h. LC-MS (Method 10-90) showed product was present (Rt 3.41 min; m/z 649.4 [M+H]+. Saturated aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the title compound (345 mg containing some solvent residue, ca. 100% yield) as a brown oil.

後処理

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-cf79d9c8dac248948ab4e5a6054ef3e1
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394275B2

反応ノート

読み込み中…

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