Methyl iodide → 526-31-8

HRID 1280091

반응식

HRID 1280091 반응식
O[C:2]1[CH:16]=[C:15]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:20]>CN(C=O)C>[CH3:20][NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]1[C:15]2[C:5](=[CH:4][CH:3]=[CH:2][CH:16]=2)[NH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 439280Oxitriptan

생성물 1

HCID 160511526-31-8

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The protected tryptophan derivative from above (0.573 g, 1.00 mmol) was dissolved in DMF (3 mL) and the solution cooled in ice. Sodium hydride (60% oil dispersion, 0.048 g, 1. 2mmol) was added and the mixture stirred for 30 min. Iodomethane (0.093 mL, 1.5 mmol) was added and stirring continued for an additional hour. The reaction was then quenched with 10% citric acid (2 mL) and water (25 mL), and extracted with Et2O (100 mL). The extract was dried (MgSO4) and concentrated, and the residue purified by flash chromatography (20-30% EtOAc 1 hexane as eluent) to give the desired N-methyltryptophan derivative (0.284 g).

후처리

  1. temperaturethe solution cooled in ice
  2. stirringstirring
  3. waitcontinued for an additional hour
  4. customThe reaction was then quenched with 10% citric acid (2 mL) and water (25 mL)
  5. extractionextracted with Et2O (100 mL)
  6. dry with materialThe extract was dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue purified by flash chromatography (20-30% EtOAc 1 hexane as eluent)

출처 및 근거

ORD 기록
ord-595fbb050cea47628560ca44e70c8f10
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448281B1

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