O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1) → methyl (2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-(2-methylpropoxyimino)acetate

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Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:17])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([Cl:16])[CH:7]=1)=O.Cl.[CH2:19]([O:23][NH2:24])[CH:20]([CH3:22])[CH3:21]>CO>[CH3:1][O:2][C:3](=[O:17])/[C:4](/[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([Cl:16])[CH:7]=1)=[N:24]/[O:23][CH2:19][CH:20]([CH3:22])[CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

(3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester (prepared as in Example 1, 90 mg, 3.26 mmol) was stirred in methanol (7 mL) and warmed in a 70° C. oil bath. O-Isobutylhydroxylamine hydrochloride (511 mg, 4.07 mmol) was added. After 3 h, the reaction mixture was allowed to cool and concentrated in vacuo. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes to 30% ethyl acetate/hexanes) afforded (E)-(3-chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid methyl ester as a white solid (395 mg, 35%): H1-NMR (400 MHz, CDCl3) δ=0.91 (6H, d, J=6.8 Hz), 2.04 (1H, m), 3.30 (3H, s), 3.91 (3H, s), 4.10 (2H, d, J=6.8 Hz), 7.50 (1H, dd, J=8.2 Hz, J=1.6 Hz), 7.61 (1H, d, J=1.6 Hz), 8.18 (1H, d, J=8.2 Hz).

Aufarbeitung

temperatureto cool
concentrationconcentrated in vacuo
customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes to 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-518a26f31426471797fef7d09fc28d62
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07902248B2

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