Methyl iodide → HCID 54519475, 화합물

HRID 412111노트

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HRID 412111 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 54519475HCID 54519475, 화합물수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-31fdc90bf8804fa1933f90b887fb4714
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562842B2

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