Hydrochloric Acid → 3-(4-{[6-(Benzyl{(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide

HRID 2118189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118189
Cl.[CH2:2]([N:9]([CH2:31][C@@H:32]([C:34]1[CH:45]=[CH:44][C:37]2[O:38]C(C)(C)[O:40][CH2:41][C:36]=2[CH:35]=1)[OH:33])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([N:9]([CH2:31][C@H:32]([OH:33])[C:34]1[CH:45]=[CH:44][C:37]([OH:38])=[C:36]([CH2:41][OH:40])[CH:35]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 691986253-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide

Produkt 1

HCID 691969033-(4-{[6-(Benzyl{(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamideAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Hydrochloric acid (80 ml, 1M) was added dropwise to a stirred solution of 3-{4-[(6-{benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide (20 g) in ethanol (100 ml) at 0° C. Upon complete addition the mixture was stirred at 5° C. for 1 h before being allowed to warm to room temperature. A portion (50 ml) of the ethanol was removed under reduced pressure and the remaining mixture was diluted with ethyl acetate (250 ml). The mixture was then washed with water (100 ml), saturated sodium bicarbonate solution (100 ml) and brine (100 ml) before being dried over anhydrous Na2SO4. The suspension was filtered and concentrated under reduced pressure to give the title compound (16 g) as an oil. LC R=4.02 min, δ (DMSO-d6) 9.15 (1H, s), 7.65 (1H, s), 7.64 (1H, d, J 8.8 Hz), 7.45 (2H, m), 7.27 (8H, m), 6.94 (1H, dd, J 8.2 Hz), 6.67 (1H, d, J 8.2 Hz), 4.92 (1H, t, J 5.7 Hz), 4.67 (1H, s), 4.56 (1H, m), 4.45 (2H, d, J 5.7 Hz), 3.61 (2H, m), 3.34 (2H, t, J 6.3 Hz), 3.28 (2H, t, J 6.2 Hz), 2.66 (2H, m), 2.50 (2H, m), 2.39 (2H, m), 1.61 (2H, m), 1.50 (2H, m), 1.39 (4H, m), 1.16 (4H, m).

Aufarbeitung

  1. additionUpon complete addition the mixture
  2. temperatureto warm to room temperature
  3. customA portion (50 ml) of the ethanol was removed under reduced pressure
  4. additionthe remaining mixture was diluted with ethyl acetate (250 ml)
  5. washThe mixture was then washed with water (100 ml), saturated sodium bicarbonate solution (100 ml) and brine (100 ml)
  6. dry with materialbefore being dried over anhydrous Na2SO4
  7. filtrationThe suspension was filtered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-589c1db7dcf14d0c949954b639e939cb
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442836B2

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