Methyl iodide → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide

HRID 469503ノート

反応式

HRID 469503 の反応式
[I:1][CH3:2].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH:23][C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12](=[O:22])[O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:7][CH:6]=1>CCOC(C)=O>[I-:1].[CH2:30]([O:29][C:27]([C:26]1[CH:25]=[C:24]([NH:23][CH:11]([C:8]2[CH:9]=[N:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[C:12]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH3:2])([CH2:17][CH2:18]3)[CH2:15]2)=[O:22])[CH:34]=[CH:33][CH:32]=1)=[O:28])[CH3:31]

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

生成物 1

HCID 67124884(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide収率 38%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Iodomethane (7.1 μl, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide (24.3 mg, 36.7% yield).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by preparative HPLC (Eluent: CH3CN/H2O)

出典と根拠

ORDレコード
ord-411c0350a18547b3a153d38184e4c314
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

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