Potassium Carbonate → 7-[2-(4-Cyanobenzenesulfonylamino)ethyl]-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester

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Reaktionsgleichung

Br[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[C:16]([O:20][C:21]([N:23]1[CH2:30][CH:29]2[O:31][CH:25]([CH2:26][NH:27][CH2:28]2)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH:25]2[O:31][CH:29]([CH2:28][N:27]([CH2:2][CH2:3][NH:4][S:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:26]2)[CH2:30]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A suspension of N-(2-bromoethyl)-4-cyanobenzenesulfonamide (5 g, 0.017 mol; see step (i) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (3.96 g, 0.0173 mol; see WO 01/28992) and potassium carbonate (3.6 g, 0.025 mol) in acetonitrile (50 mL) was stirred at 60° C. overnight. The reaction mixture was filtered and the solvent concentrated under reduced pressure to yield the crude product, which was purified by column chromatography (using methanol in chloroform as the eluent) to yield (5 g) of the sub-title compound as pale yellow solid.

Aufarbeitung

filtrationThe reaction mixture was filtered
concentrationthe solvent concentrated under reduced pressure
customto yield the crude product, which
customwas purified by column chromatography (

Quellen und Nachweise

ORD-Eintrag: ord-1922c865ab9649e2aa5618061451df08
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07648985B2

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