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

HRID 36127

반응식

HRID 36127 반응식
[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.CN.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]

참가 물질

7

반응물 5

HCID 702EthanolHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 13041PentafluorophenolHCID 7020841N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine

생성물 1

HCID 22851210N-Boc-4-cyanophenylalanine-N-methylamide수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 methylamine 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a67bf3e8d4a2491c9a876d6e5cb62b11
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412145

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