Hydrochloric Acid → {3-[(Pyridine-3-sulfonylamino)-methyl]-phenyl}acetic acid methyl ester

HRID 842746ノート

反応式

HRID 842746 の反応式
Cl.[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1.C(NC(C)C)(C)C.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=1.Cl>ClCCl>[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][S:28]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)(=[O:30])=[O:29])[CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 21185371Methyl 2-[3-(aminomethyl)phenyl]acetate hydrochloride

生成物 1

HCID 54480791{3-[(Pyridine-3-sulfonylamino)-methyl]-phenyl}acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (3-aminomethyl-phenyl)-acetic acid methyl ester hydrochloride (0.56 g) and diisopropylamine (2.2 mL) in 10 mL dichloromethane was added pyridine-3-sulfonyl chloride (0.601 g, 2.83 mmol) and the reaction was stirred at room temperature for 16 h. Aqueous 1N HCl was added and the solution was extracted with CH2Cl2. The organic solution was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound. Purification via flash chromatography on silica gel (2:1 hexanes: EtOAc) afforded the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.71 (d, 1H), 8.04 (d, 1H), 7.37 (m, 1H), 7.05-7.24 (m, 4H), 5.87 (bs, 1H), 4.14 (s, 1H), 2H), 3.62 (s, 3H), 3.52 (s, 2H).

後処理

  1. extractionthe solution was extracted with CH2Cl2
  2. washThe organic solution was washed with saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1d4cfda45efb4b759715795e1a543993
出典データセット
uspto-grants-2002_04
特許番号
US06376502B1

反応ノート

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