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 2117684ノート

反応式

HRID 2117684 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bd05d36bb5d442f6acad5d30cb871216
出典データセット
uspto-grants-2008_10
特許番号
US07442719B2

反応ノート

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