Hydrochloric Acid → HCID 178496282, Verbindung

HRID 1805508

Reaktionsgleichung

[N:1]([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:22][O:23][CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28].CC([O-])=O.[Na+]>O.CO>[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][N:1]=[C:26]([C:25](=[O:31])[CH2:24][O:23][CH3:22])[C:27]([O:29][CH3:30])=[O:28])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of NaNO2 (2.07 g, 30 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 4-(benzyloxy)-2-fluoroaniline (5.43 g, 25 mmol) and 6 M HCl aqueous solution (25 mL, 150 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (3.24 mL, 24 mmol) and NaOAc (12.3 g, 150 mmol) in MeOH (50 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (8.48 g, 91% yield) as a yellow solid: 1H NMR (300 MHz, CDCl3): δ ppm 3.500 (3H×0.46, s), 3.502 (3H×0.54, s), 3.88 (3H×0.54, s), 3.92 (3H×0.46, s), 4.65 (2H×0.46, s), 4.68 (2H×0.54, s), 5.06 (2H×0.54, s), 5.07 (2H×0.46, s), 6.75-6.86 (2H, m), 7.32-7.44 (5H, m), 7.53 (1H×0.46, t, J=9.0 Hz), 7.76 (1H×0.54, t, J=9.0 Hz), 13.12 (1H×0.46, brs), 15.13 (1H×0.54, brs).

Aufarbeitung

extractionextracted with AcOEt
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from hexane/AcOEt

Quellen und Nachweise

ORD-Eintrag: ord-eebeb4d31cb34ce2aa1335d3535c25a4
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08354411B2

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