Methyl iodide → N-methyl-L-tryptophan

HRID 1018270ノート

反応式

HRID 1018270 の反応式
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

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 439280Oxitriptan

生成物 1

HCID 160511N-methyl-L-tryptophan

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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, 1.2 mmol) 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/hexane as eluent) to give the desired N-methyltryptophan derivative (0.284g).

後処理

  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/hexane as eluent)

出典と根拠

ORDレコード
ord-f490b21ab9e64a7581a4f9d22a7a0000
出典データセット
uspto-grants-2002_11
特許番号
US06479508B1

反応ノート

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