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

HRID 525910笔记

反应方程式

HRID 525910 反应方程式
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]

参与物

4

反应物 2

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

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

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

后处理

  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

来源与证据

ORD记录
ord-8c9c372ea31f49a8b15d451aeeca95da
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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