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

HRID 2117681노트

반응식

HRID 2117681 반응식
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

참가 물질

4

반응물 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

생성물 1

HCID 691969033-(4-{[6-(Benzyl{(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide수율 85.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
5 °C

실험 절차

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 RT=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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f33ea4d0feb455bb11bd28e06b45544
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442719B2

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