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Ethyl Acetate → 3-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-1H-pyrazin-2-one oxalate

HRID 890090
ノート
印刷プレビュー

反応式

HRID 890090 の反応式
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[C:13]([O:18]C)=[N:14][CH:15]=[CH:16][N:17]=2)[CH2:7]1.[C:24](=[O:27])([OH:26])[O-].[Na+].[C:29]([O:32]CC)(=[O:31])C>C(O)C.Cl.C(OCC)(=O)C>[C:29]([OH:32])(=[O:31])[C:24]([OH:26])=[O:27].[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[C:13](=[O:18])[NH:14][CH:15]=[CH:16][N:17]=2)[CH2:7]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 222479393-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-2-methoxypyrazine

生成物 1

HCID 222485423-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-1H-pyrazin-2-one oxalate収率 56%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 21866389
Hydrogen chloride-ethyl acetate
溶媒

反応条件

温度
60 °C

実験手順

After dissolving 245 mg of 3-[3-(2-fluorophenoxymethyl)pyrrolidino]methyl-2-methoxypyrazine in 5 ml of ethanol, 15 ml of 4N hydrogen chloride/ethyl acetate was added, and the mixture was heated to reflux for 8 hours and then stirred overnight at 60° C. Aqueous sodium bicarbonate solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol). This was dissolved in a small amount of ethanol, and then 47 mg of oxalic acid anhydrous and ethyl acetate were added and the precipitate was filtered out to obtain the title compound (171 mg, 56% yield).

後処理

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 8 hours
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol)
  8. dissolutionThis was dissolved in a small amount of ethanol
  9. addition47 mg of oxalic acid anhydrous and ethyl acetate were added
  10. filtrationthe precipitate was filtered out

出典と根拠

ORDレコード
ord-96db85a7d9074514867b989e7018794a
出典データセット
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06995144B2

反応ノート

読み込み中…

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