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

HRID 551961ノート

反応式

HRID 551961 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:32]=[CH:31][C:16]([CH2:17][N:18]([CH3:30])[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:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:32]=[CH:31][C:16]([CH2:17][N:18]([CH3:30])[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

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554550Methyl 5-[(4-[(4-butylphenyl)ethynyl]benzyl}(methyl)amino]-2-fluorobenzoate

生成物 1

HCID 115897305-[{4-[(4-Butylphenyl)ethynyl]benzyl}(methyl)amino]-2-fluorobenzoic acid収率 59.4%

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}(methyl)amino]-2-fluorobenzoate (66 mg; 0.15 mmol) in 3 mL of anhydrous THF were added. Lithium Hydroxide monohydrate (65 mg; 1.54 mmol) and water (1 mL). The reaction mixture was stirred under micro waves at 100° C. for 3500 s. Then an aqueous solution of HCl was added; the residue was extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, filtrated and concentrated to give 37 mg of the title compound as a white solid. HPLC, Rt: 5.66 min (purity=93.20%). LC/MS, M−(ESI): 414.5. 1H NMR (CDCl3) δ: 7.40 (m, 4H), 7.31 (s, 1H), 7.20 (m, 4H), 6.92 (t, 1H), 6.75 (m, 1H), 4.42 (s, 2H), 2.92 (s, 3H), 2.54 (t, J=7.7 Hz, 2H), 1.50 (m, 2H), 1.25 (m, 2H), 0.82 (t, J=7.5 Hz, 3H).

後処理

  1. extractionthe residue was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9442a8760fdd4e8da3a5d9db927cb89e
出典データセット
uspto-grants-2011_05
特許番号
US07947851B2

反応ノート

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