Sodium Chloride → 3-(2-Ethoxyethanoyl)-4-benzyloxazolidin-2-one

HRID 585008

Reaktionsgleichung

[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[CH2:25]([O:27][CH2:28][C:29](Cl)=[O:30])[CH3:26].[Cl-].[Na+]>C1COCC1>[CH2:25]([O:27][CH2:28][C:29]([N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:30])[CH3:26]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

36.7 g (207 mmol) of (S)-4-benzyloxazolidin-2-one in 800 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is cooled to −78° C. and 83 ml (207 mmol) of 2.5M n-butyllithium hexane are added dropwise. 30 minutes later, 25.4 g (207 mmol) of ethoxyacetyl chloride obtained in Example 81(b) are added, at −78° C. The reaction medium is stirred for 24 hours and then poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. After purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product are obtained in the form of an orange-colored oil.

Aufarbeitung

extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
customevaporated
customAfter purification by chromatography on a column of silica
washeluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product
customare obtained in the form of an orange-colored oil

Quellen und Nachweise

ORD-Eintrag: ord-87b9334d6a78453ab58a80b7a1cff62e
Quelldatensatz: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06927228B2

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