Potassium Iodide → HCID 67246826, compound

HRID 1027572Notes

Reaction equation

HRID 1027572 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][O:11][NH:10][C:9]1=[O:13])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:24][CH2:25][OH:26]>C(#N)C>[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]1[CH2:12][O:11][N:10]([CH2:24][CH2:25][OH:26])[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 5225473HCID 5225473, compound

Product 1

HCID 67246826HCID 67246826, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3-Oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester (0.2 g, prepared from (D)-cycloserine as described in Chem. Pharm. Bull. 2002, 50(4) 554-557) was dissolved in acetonitrile (20 ml), then potassium carbonate (0.69 g), potassium iodide (0.175 g) and 2-bromoethanol (0.137 g) were added. The reaction was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and then dried over sodium sulphate. The solvent was removed in vacuo and the crude product was purified by column chromatography (eluent cyclohexane/ethyl acetate) to afford ((R)-2-(2-hydroxyethyl)-3-oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester as a yellow solid. LCMS (method A) 1.05 min, MH+ 259; 1H-NMR (CDCl3, 400 MHz): 5.55 (br s, 1H), 4.65 (m, 2H), 4.10 (t, 1H), 3.80 (m, 1H), 3.20 (br s, 1H), 1.50 (s, 9H), 1.20 (m, 3H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by column chromatography (eluent cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-39d210b0114b425191b1e6f32d60a3b4
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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