Diethyl Ether → 3-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide

HRID 2117684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117684
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([OH:14])[CH3:13])=[CH:11][C:5]=2[CH2:4][O:3]1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[C:30]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.C(N(CC)[CH:42]([CH3:44])[CH3:43])(C)C.[C:47](#[N:49])[CH3:48].[CH2:50](OCC)[CH3:51]>O>[CH2:47]([N:49]([CH2:13][C@@H:12]([C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([CH3:1])([CH3:15])[O:3][CH2:4][C:5]=2[CH:11]=1)[OH:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[C:30]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1)[C:48]1[CH:43]=[CH:42][CH:44]=[CH:51][CH:50]=1

Komponenten

7

Edukt 5

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 115093953-{3-[(7-Bromoheptyl)oxy]propyl}benzenesulfonamideHCID 692850371-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Produkt 1

HCID 691987473-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (1R)-2-benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (55.8 g), 3-{3-[(7-bromoheptyl)oxy]propyl}benzenesulfonamide (63.65 g), N,N-diisopropylethylamine (55 ml) and acetonitrile (200 ml) was stirred and heated under N2 at reflux for ca 21 h. The mixture was cooled to room temperature then diethyl ether (1000 ml) and water (500 ml) were added and the mixture stirred. The organic phase was washed with water (500 ml), then saturated brine (500 ml) and dried (Na2SO4). The solution was concentrated and the product purified by chromatography on flash silica gel (1000 g), eluting with petroleum ether:ethyl acetate (ratios ranging successively from 4:1 to 1:1) to give the title compound (97.7 g)—LC RT=1.54 min. δ (DMSO-d6)—7.75 (2H, m), 7.45 (1H, t, J 8 Hz), 7.4 (1H, m), 7.35 (2H, s), 7.25 (5H, m), 7.05 (1H, d, J 8.5 Hz), 7.0 (1H, s), 6.7 (1H, d, J 8.5 Hz), 4.9 (1H, br s), 4.78 (2H, s), 4.6 (1H, m), 3.65 (1H, d, J 13.8 Hz), 3.55 (1H, d, J 13.8 Hz), 3.4 (1H, br s), 3.3 (4H, m), 2.7 (2H, m), 2.55 (2H, m), 2.4 (2H, m), 1.85 (2H, m), 1.45 (8H, m), 1.35 (2H, m), 1.25 (2H, m), 1.15 (4H, m).

Aufarbeitung

  1. temperatureheated under N2
  2. temperatureat reflux for ca 21 h
  3. stirringthe mixture stirred
  4. washThe organic phase was washed with water (500 ml)
  5. dry with materialsaturated brine (500 ml) and dried (Na2SO4)
  6. concentrationThe solution was concentrated
  7. customthe product purified by chromatography on flash silica gel (1000 g)
  8. washeluting with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-bd05d36bb5d442f6acad5d30cb871216
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442719B2

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