Hydrochloric Acid → Vilanterol

HRID 503093ノート

反応式

HRID 503093 の反応式
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]

参加物

6

反応物 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

生成物 1

HCID 10184665Vilanterol収率 73.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a57dcc2be8294ec2a3dacc8f065dc7df
出典データセット
uspto-grants-2010_08
特許番号
US07776895B2

反応ノート

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