Methyl iodide → HCID 54519475, compound

HRID 1356520Notes

Reaction equation

HRID 1356520 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7].CI.[H-].[Na+].[C:25](OCC)(=O)C>C1COCC1.O>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:16][CH:17]([CH3:18])[CH3:19])[N:5]([CH3:25])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 54205230HCID 54205230, compound

Product 1

HCID 54519475HCID 54519475, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(2-pyridinylmethoxycarbonyl)-L-leucine methyl ester (490 mg, 1.75 mmol) was dissolved in THF (7.0 mL) and methyl iodide (0.435 mL, 6.99 mmol) was added. The reaction mixture was cooled to 0° C. in a flask protected from moisture. Sodium hydride dispersion (236 mg, 2.62 mmol) was added cautiously and the suspension was stirred for 5 hours at room temperature. Ethyl acetate was then added, followed by water, dropwise. The solution was concentrated in vacuo, and the oily residue partitioned between ether and water. The organic layer was washed with saturated aqueous NaHCO3 and the combined aqueous extracts acidified to pH 3 with citric acid. The product was extracted with ethyl acetate, the extract was washed with water, 5% aqueous sodium thiosulfate and water, dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography on silca gel (ethyl acetate/hexane, 3:1) to give a yellow oil (235 mg, 46%). MS (ESI): 295.4 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe oily residue partitioned between ether and water
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. extractionThe product was extracted with ethyl acetate
  5. washthe extract was washed with water, 5% aqueous sodium thiosulfate and water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography on silca gel (ethyl acetate/hexane, 3:1)

Sources & evidence

ORD record
ord-3078ffb3df57464cb9b41626d3ae3fca
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

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