Methylhydrazine → (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(aminooxy)succinate

HRID 525910ノート

反応式

HRID 525910 の反応式
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C@@H:13]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:15].CNN>ClCCl>[NH2:3][O:12][C@@H:13]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:15]

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 86732776(S)-4-tert-butyl 1-(4-methoxybenzyl) 2-((1,3-dioxoisoindolin-2-yl)oxy)succinate

生成物 1

HCID 86732775(S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(aminooxy)succinate収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-((1,3-dioxoisoindolin-2-yl)oxy)succinate (68 g, 149 mmol) in Dichloromethane (DCM) (500 mL) was added methylhydrazine (7.86 mL, 149 mmol) dropwise at 0° C. over 30 min. The mixture was allowed to warm to rt and stirred at rt for 1 h. LCMS indicated completion of the reaction. The insoluble material was removed by filtration and the filtrate was concentrated and diluted with toluene. The resulting precipitate was removed by filtration again and the filtrate was concentrated to afford crude (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(aminooxy)succinate (47 g, 144 mmol, 97% yield) as a pale yellow oil. The product was used in next step without further purification. LCMS: (M+H)+: 326.1

後処理

  1. customcompletion of the reaction
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additiondiluted with toluene
  5. customThe resulting precipitate was removed by filtration again
  6. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-8c9c372ea31f49a8b15d451aeeca95da
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

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