Ethanol → N-Boc-4-cyanophenylalanine-N-methylamide

HRID 1463548

反応式

HRID 1463548 の反応式
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].FC1C(O)=C(F)C(F)=C(F)C=1F.[CH3:34][N:35]1CCOCC1.C(O)C>C(Cl)Cl>[CH3:34][NH:35][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

6

反応物 4

HCID 702EthanolHCID 79724-MethylmorpholineHCID 13041PentafluorophenolHCID 7020841N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine

生成物 1

HCID 22851210N-Boc-4-cyanophenylalanine-N-methylamide収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of N-Boc-4-cyanophenylalanine (1.92 g, 6.6 mmol) and pentafluorophenol (2.43 g, 13.2 mmol) in CH2Cl2 (30 ml) at 0° C. was treated with 4-methylmorpholine (0.74 g, 7.3 mmol). After stirring the reaction mixture for 3 hours, 8M methylazine in ethanol (15 ml, 19.8 mmol) was added and the reaction mixture left to stir at room temperature for 16 hours. The solvent was removed under pressure, the residue dissolved in CH2Cl2 (50 ml) and washed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml). The CH2Cl2 layer was dried over MgSO4 and the solvent removed under pressure to yield the title compound as a white solid (1.84 g, 92%).

後処理

  1. waitthe reaction mixture left
  2. stirringto stir at room temperature for 16 hours
  3. customThe solvent was removed under pressure
  4. dissolutionthe residue dissolved in CH2Cl2 (50 ml)
  5. washwashed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml)
  6. dry with materialThe CH2Cl2 layer was dried over MgSO4
  7. customthe solvent removed under pressure

出典と根拠

ORDレコード
ord-9949f6ba5f064ab3845911c82f62e8b6
出典データセット
uspto-grants-1994_04
特許番号
US05300674

関連ノート

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