Hydroxyamine hydrochloride → Tert-butyl 1-(3-((hydroxyimino)methyl)phenyl)ethylcarbamate
Reaktionsgleichung
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1)=O.C([O-])(=O)C.[Na+].Cl.[NH2:25][OH:26]>C1COCC1>[OH:26][N:25]=[CH:1][C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate (4.0 g, 16.0 mmol) and sodium acetate (3.3 g, 40.1 mmol) in THF (69 mL) at 0° C. was added hydroxylamine hydrochloride (1.4 g, 20.9 mmol). The reaction was allowed to warm to ambient temperature and stirred for 16 hours. The reaction was concentrated in vacuo and the residue partitioned between EtOAc and water and the layers separated. The organic layer was washed with brine (×2), dried (Na2SO4), filtered and concentrated in vacuo to give the sub-title compound as a colourless gel (4.24 g, quantitative Yield). 1H NMR (400 MHz, DMSO) δ 1.30 (d, 3H), 1.33 (d, 9H), 4.61 (dd, 1H), 7.24-7.38 (m, 2H), 7.41 (q, 2H), 7.53 (s, 1H), 8.11 (s, 1H) and 11.20 (s, 1H) ppm; MS (ES+) 265.3.
Aufarbeitung
- concentrationThe reaction was concentrated in vacuo
- customthe residue partitioned between EtOAc and water
- customthe layers separated
- washThe organic layer was washed with brine (×2)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-d133307ec5564561b23ce34fd453ab9a
- Quelldatensatz
- uspto-grants-2014_01
- Patentnummer
- US08623869B2
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