Methyl iodide → HCID 54519475、化合物

HRID 1977482ノート

反応式

HRID 1977482 の反応式
[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]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 54205230HCID 54205230、化合物

生成物 1

HCID 54519475HCID 54519475、化合物収率 46%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-346316cbf14542b5a2537405e7138d0d
出典データセット
uspto-grants-2001_05
特許番号
US06232342B1

反応ノート

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