Hydroxyamine hydrochloride → 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime

HRID 2409011ノート

反応式

HRID 2409011 の反応式
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl.[NH2:24][OH:25].CC([O-])=O.[Na+]>CO>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:24][OH:25])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898211-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone

生成物 1

HCID 1364090991-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime収率 97.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone (1.32 g, 4.2 mmol) in MeOH (50 mL) at RT was added hydroxylamine hydrochloride (877 mg, 12.61 mmol) followed by NaOAc (3.45 g, 42.0 mmol). The reaction mixture was stirred at 80° C. for 1 h then concentrated tinder reduced pressure. Water (100 mL) was added to the reaction mixture, and the mixture extracted with EtOAc (50 mL×3). The combined organic layers were concentrated under reduced pressure to afford 1.35 g (97.6%) of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime as yellow solid: MS (ESI) m/z: 320.1 [M+1]+.

後処理

  1. concentrationthen concentrated tinder reduced pressure
  2. additionWater (100 mL) was added to the reaction mixture
  3. extractionthe mixture extracted with EtOAc (50 mL×3)
  4. concentrationThe combined organic layers were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-823c9862ff26494195853edf6d603314
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

反応ノート

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