Sodium Carbonate → (S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidine-5-carboxylic acid

HRID 1640519

Reaktionsgleichung

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@@H:14]([CH2:16][OH:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:21])C.CC1(C)N([O])C(C)(C)CCC1.C([O-])([O-])=O.[Na+].[Na+]>CC(=O)OCC.O.CC#N>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@@H:14]([C:16]([OH:21])=[O:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-one (985 mg, 3.92 mmol) in 1:1 water/MeCN (20 mL) cooled to 0° C. was added diacetoxyiodobenzene (2.83 g, 2.2 eq.) and TEMPO (122 mg, 0.2 eq). The mixture was stirred at 0° C. for 30 min and at rt overnight. EA and sat. Na2CO3 were added and the phases were separated. The aq. layer was washed once more with EA and then carefully acidified with 1M HCl. The water phase was then extracted twice with EA. The combined org. layers were washed with brine and dried over MgSO4 and concentrated to afford the title intermediate as a colourless solid (847 mg, 81% yield).

Aufarbeitung

customthe phases were separated
washThe aq. layer was washed once more with EA
extractionThe water phase was then extracted twice with EA
washlayers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-77ba1dbf9cad4bb3902789dce93097a6
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08114867B2

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