Hydrochloric Acid → 5-{{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-carboxycyclopropyl) methyl]amino}-2-fluorobenzoic acid

HRID 551969

反応式

HRID 551969 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:30][CH:31]3[CH2:33][CH:32]3[C:34]([O:36]CC)=[O:35])[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].O.[OH-].[Li+].O.Cl>C1COCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:30][CH:31]3[CH2:33][CH:32]3[C:34]([OH:36])=[O:35])[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:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554524Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoate

生成物 1

HCID 116217505-{{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-carboxycyclopropyl) methyl]amino}-2-fluorobenzoic acid収率 73.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoate (340 mg; 0.63 mmol) in anhydrous THF (5 mL) were added lithium hydroxide monohydrate (64 mg; 1.54 mmol) and water (7 mL). The reaction mixture was stirred under MW at 100° C. for 2500 s. Then an aqueous solution of HCl (1N) was added, the residue was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (60 mL), dried over magnesium sulfate and the solvent was removed under reduced pressure to give 230 mg (73%) of the title compound as a white solid. HPLC, Rt: 4.99 min (purity 99.5%). LC/MS: M−(ESI): 498.2, 1H NMR (MeOD) δ: 7.46 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.3 Hz, 2H), 7.29 (m, 3H), 7.21 (d, J=7.9 Hz, 2H), 4.66 (s, 2H), 3.44 (m, 1H), 2.65 (t, J=7.5 Hz, 2H), 1.65 (m, 3H), 1.35 (m, 3H), 1.15 (m, 1H), 0.95 (m, 4H), 3.59 (m, 1H), 7.05 (m, 2H).

後処理

  1. extractionthe residue was extracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with brine (60 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-03dfc9bda7f34860b68813fecd5bc4a3
出典データセット
uspto-grants-2011_05
特許番号
US07947851B2

関連ノート

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