Hydrochloric Acid → 4-Hydroxy-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

HRID 1827532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827532
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C3CCCCO3)=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.O>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:30][CH:31]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 221372724-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Produkt 1

HCID 221373084-Hydroxy-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide in methanol (20 mL) was added 1N HCl (5 mL). After stirring for 2 hr., water was added and the aqueous solution was washed with methylene chloride (3×). The combined organic solutions were washed with saturated aqueous sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated. The residue was purified via radial chromatography using a solvent gradient (methylene chloride to 10% methanol/methylene chloride) to provide the title compound. 1H NMR (CD3OD) δ 7.44 (d, 2H, J=8.0 Hz), 6.96 (d, 2H, J=8.0 Hz), 6.85–6.74 (m, 4H), 6.73 (d, 2H, J=8.0 Hz), 6.58 (d, 2H, J=8.0 Hz), 4.55 (s, 2H), 4.02 (t, 2H, J=5.6 Hz), 2.89 (t, 2H, J=5.6 Hz), 2.67 (bs, 4H), 1.81 (bs, 4H).

Aufarbeitung

  1. washthe aqueous solution was washed with methylene chloride (3×)
  2. washThe combined organic solutions were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via radial chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15a21f5a88534f90a032271c2e91fc2a
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053212B2

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