Iodoethane → N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanine

HRID 1486097ノート

反応式

HRID 1486097 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14](I)[CH3:15].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:14][CH3:15])[C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 85082Tert-butoxycarbonylalanine

生成物 1

HCID 71423142N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanine収率 87.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of (S)-2-(tert-butoxycarbonylamino)propanoic acid (0.7 g, 3.7 mmol) and ethyl iodide (2.6 ml, 32.2 mmol) in THF (10 ml) was added sodium hydride (60% w/w dispersion in mineral oil, 576 mg, 14.4 mmol). The reaction was sealed and stirred at 60° C. overnight, then partitioned between EtOAc and H2O. The aqueous layer was acidified to pH 4 with citric acid solution and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to provide (S)-2-(tert-butoxycarbonyl(ethyl)amino)propanoic acid (700 mg, 87%) as an oil.

後処理

  1. customThe reaction was sealed
  2. custompartitioned between EtOAc and H2O
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3c9421c99ef048abab6d79f89116cb5b
出典データセット
uspto-grants-2016_08
特許番号
US09422331B2

反応ノート

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