m-Chloroperbenzoic acid → (S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide

HRID 931775Notizen

Reaktionsgleichung

[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:24])=[N:7]2.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>ClCCl>[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:24])=[N+:7]2[O-:33]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred solution of (S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate (5H) (248 mg, 0.63 mmol) in dichloromethane (8 mL) was added a solution of mCPBA (283 mg, 77%, 1.26 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour before quenched with NaHCO3 solution. The mixture was extracted with DCM (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (212 mg, 82%). LCMS-ESI+ (m/z): 410.2, 412.2 (M+H)+.

Aufarbeitung

custombefore quenched with NaHCO3 solution
extractionThe mixture was extracted with DCM (30 mL)
washwashed with NaHCO3 solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe obtained residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-88887a003fb346c0a6b8a510ff53dc66
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09296758B2

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