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

HRID 1511780

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(OC[C@H]1OC1)(=[O:23])CCC.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)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:23])=[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 (enantiomeric antipode of intermediate 1.iii), prepared from (S)-glycidyl butyrate, 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 separated. The aq. layer was washed once more with EA and then carefully acidified with 1M aq. HCl. The aq. phase was then extracted 2× with EA. The combined org. layers were washed with brine and dried over MgSO4 and concentrated to afford the desired intermediate as colourless solid (847 mg, 81%).

Aufarbeitung

customthe phases separated
washThe aq. layer was washed once more with EA
extractionThe aq. phase was then extracted 2× with EA
washlayers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-a9a04af59b57411bbe838ee8d77f2a07
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08217029B2

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