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Hydrochloric Acid → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-hydroxyphenyl)-3-phenylacrylamide

HRID 884067
ノート
印刷プレビュー

反応式

HRID 884067 の反応式
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:30]=[CH:29][C:28]([O:31]COC)=[CH:27][CH:26]=2)=[C:15](\[CH:22]2[CH2:24][CH2:23]2)/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.O1CCOCC1.O>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[C:15](\[CH:22]2[CH2:24][CH2:23]2)/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68732008(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylamide

生成物 1

HCID 42603087(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-hydroxyphenyl)-3-phenylacrylamide収率 88%

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 8 (70 mg, 0.144 mmol) in MeOH (3 ml) was added 4N HCl in 1,4-dioxane (0.4 ml) under ice cooling, and the mixture was stirred at room temperature for 3 h. A solution of NaHCO3 in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was crystallized with Et2O to give 9 (88%). 9: colorless powder; 1H-NMR (CD3OD) δ 0.42 (2H, m), 0.73 (2H, m), 1.99 (1H, m), 2.35 (6H, s), 2.77 (2H, t, J=5.4 Hz), 4.10 (2H, t, J=5.4 Hz), 6.47 (2H, d, J=8.8 Hz), 6.91 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.1 Hz), 7.06 (2H, m), 7.13-7.23 (3H, m), 7.56 (2H, d, J=9.3 Hz). HRMS calcd for C28H31N2O3 [M+H]+: 443.2335. Found: 443.2353.

後処理

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residual solid was crystallized with Et2O

出典と根拠

ORDレコード
ord-a51ddd4754e34089823b1e602bf866d8
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08236987B2

反応ノート

読み込み中…

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