Cesium carbonate → (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066806

Reaktionsgleichung

[Cl:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.Br[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1>[Cl:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)[CH2:4]1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

A mixture of (5R)-5-(chloromethyl)-1,3-oxazolidin-2-one (2.15 g, INTERMEDIATE 5), 2-bromo-5-chloropyridine (3.05 g), cesium carbonate (20.67 g), bispalladium tribenzylideneacetone (2.18 g) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.07 g) in 16 ml of dioxane was stirred at 85° C. for 12 h. The sample was then cooled to room temperature, and purified was purified via column chromatography (2×) on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 60% ethyl acetate in hexanes (over 10 column volumes), and held at 60% ethyl acetate for 4 column volumes to provide the title compound (2.32 g, 59%). Mass spectrum (ESI) 249.0 (M+2).

Aufarbeitung

temperatureThe sample was then cooled to room temperature
custompurified
customwas purified via column chromatography (2×) on a Biotage Horizon 65i column
washeluting with 0% ethyl acetate in hexanes (1 column volume)

Quellen und Nachweise

ORD-Eintrag: ord-0da5cc8feee14cd0a4244e17f220b3d8
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08293721B2

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