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

HRID 1640506

Reaction equation

HRID 1640506 reaction equation
O.[CH3:2][C:3]#[N:4].C([O:8][C:9]1[C:10]([O:16][C:17](=O)[CH3:18])=[C:11](I)C=C[CH:14]=1)(=O)C.CC1(C)N([O])C(C)(C)CCC1.[C:31]([O-:34])([O-:33])=O.[Na+].[Na+].C[C:38](=[O:42])[O:39][CH2:40][CH3:41]>>[O:8]1[C:9]2[CH:14]=[CH:2][C:3]([N:4]3[CH2:41][C@@H:40]([C:31]([OH:34])=[O:33])[O:39][C:38]3=[O:42])=[CH:11][C:10]=2[O:16][CH2:17][CH2:18]1

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2724126TempoHCID 18373917Acetonitrile--water (1/1)HCID 21865429Bis(acetoxy)iodobenzene

Product 1

HCID 66736285(S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidine-5-carboxylic acidYield 81%

Conditions

Temperature
0 °C

Procedure

To a solution of intermediate 1.i (985 mg, 3.92 mmol) in 1:1 water/MeCN (20 mL) cooled to 0° C. was added diacetoxyiodobenzene (2.83 g, 8.62 mmol)) and TEMPO (122 mg, 0.78 mmol). 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 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 acid as a white solid (847 mg, 81% yield).

Workup

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

Sources & evidence

ORD record
ord-4d017f3835a54fb79dc7e3848f99ab96
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Linked notes

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