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

HRID 1955030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955030
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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, 2H), 3.62 (s, 3H), 3.52 (s, 2H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0367acb5e49a449fb34f8d78b1934a3f
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124314

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