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Ethyl Acetate → 5-{[4-[(4-Butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoic acid

HRID 551954
ノート
印刷プレビュー

反応式

HRID 551954 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26]C)=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CCOC(C)=O>CCO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
参加物反応条件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 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67170689Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoate

生成物 1

HCID 117073745-{[4-[(4-Butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoic acid収率 86%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoate (541 mg; 1.08 mmol) was dissolved in 10 mL of EtOH and sodium hydroxide (649.63 μl; 5.00 M, 3.25 mmol) was added. The reaction mixture was stirred at 65° C. for 2h30. The reaction mixture was allowed to cool down and EtOAc (50 mL) was added. The organic layer was washed three times with HCl (1M), dried over MgSO4, filtered and concentrated under reduced pressure to afford 450 mg (86%) of the title compound as a yellow solid. HPLC, Rt: 5.97 min (purity: 98.9%); LC/MS M+(ESI): 486.2, M−(ESI)=484.0; 1H NMR (CDCl3) δ: 7.44 (m, 4H), 7.32 (m, 1H), 7.20 (d, J=9.8 Hz, 2H,), 7.14 (d, J=8.3 Hz, 2H), 6.97 (m, 1H), 6.91-6.75 (m, 1H), 4.48 (s, 2H), 3.42 (m, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.65-1.46 (m, 4H), 1.40-1.28 (m, 2H), 0.99-0.87 (m, 12H).

後処理

  1. temperatureto cool down
  2. washThe organic layer was washed three times with HCl (1M)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-be20ad64d33640c29819b06c7b7a7926
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947851B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート