Sodium Carbonate → (S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidine-5-carboxylic acid
Reaction equation
[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]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-77ba1dbf9cad4bb3902789dce93097a6
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114867B2
Reaction notes
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