Dimethylformamide → Boc-L-phenylalanine methyl ester

HRID 617636ノート

反応式

HRID 617636 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])O.[K+].CN(C)C=O.CI>O>[CH3:20][O:18][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 516893Potassium Bicarbonate

生成物 1

HCID 9882138Boc-L-phenylalanine methyl ester収率 97.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of N-tert-butoxycarbonylphenylalanine (13.3 g, 50.0 mmol), potassium hydrogencarbonate (10.0 g, 100 mmol) and N,N-dimethylformamide (80 mL) was added methyl iodide (5 mL, 80 mmol). The resulting mixture was stirred at room temperature for 5 h, and water (200 mL) was added. The mixture was extracted with ethyl acetate-benzene (1:1), and the organic layer was washed successively with water, 5% aqueous sodium sulfite solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was separated and purified by silica gel column chromatography (hexane-ethyl acetate, 90:10) to give 13.6 g (96%) of N-tert-butoxycarbonylphenylalanine methyl ester as a colorless oil.

後処理

  1. extractionThe mixture was extracted with ethyl acetate-benzene (1:1)
  2. washthe organic layer was washed successively with water, 5% aqueous sodium sulfite solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was separated
  6. custompurified by silica gel column chromatography (hexane-ethyl acetate, 90:10)

出典と根拠

ORDレコード
ord-7bd697ad834a46c4a5ca553acd29ef1c
出典データセット
uspto-grants-1999_09
特許番号
US05948785

反応ノート

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