Hydrochloric Acid → Vilanterol

HRID 503093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503093
Cl.[Cl:2][C:3]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:4]=1[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]2[O:28]C(C)(C)[O:26][CH2:25][C:24]=2[CH:31]=1)[OH:19].C(=O)(O)[O-].[Na+].ClCCl>C(O)C>[Cl:2][C:3]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:4]=1[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]([OH:28])=[C:24]([CH2:25][OH:26])[CH:31]=1)[OH:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 46834265(1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Produkt 1

HCID 10184665VilanterolAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1N HCl (295 mL) was added to a solution of (R)-2-{6-[2-(2,6-dichlorobenzyloxy)-ethoxy]-hexylamino}-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-ethanol (52 g, 0.099 mol) in ethanol (312 mL), and the reaction stirred at ambient temperature for 1.5 h. Saturated sodium bicarbonate solution (500 mL) was added followed by dichloromethane (500 mL). The aqueous layer was separated and extracted with further dichloromethane (500 mL). The combined organic solutions were washed with water/brine mixture (500 mL/100 mL), then evaporated. The residue (50 g) was chromatographed on silica (800 g, Biotage) eluting with a dichloromethane/ethanol/ammonia mixture (50/8/1), to afford the title compound as an oil (35.2 g)−LC RT=4.1 min.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with further dichloromethane (500 mL)
  3. washThe combined organic solutions were washed with water/brine mixture (500 mL/100 mL)
  4. customevaporated
  5. customThe residue (50 g) was chromatographed on silica (800 g, Biotage)
  6. washeluting with a dichloromethane/ethanol/ammonia mixture (50/8/1)

Quellen und Nachweise

ORD-Eintrag
ord-a57dcc2be8294ec2a3dacc8f065dc7df
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776895B2

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