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

HRID 525910노트

반응식

HRID 525910 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-8c9c372ea31f49a8b15d451aeeca95da
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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