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

HRID 525910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525910
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8c9c372ea31f49a8b15d451aeeca95da
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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