Trimethylsilyl iodide → (S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-5-hydroxy-isoindole-1,3-dione

HRID 532119노트

반응식

HRID 532119 반응식
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:30])[N:5]([C@@H:13]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=1)[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:6]2=[O:12].I[Si](C)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:30])[N:5]([C@@H:13]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=1)[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:6]2=[O:12]

참가 물질

5

반응물 2

HCID 85247Trimethylsilyl iodideHCID 68088703(S)-4-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-5-hydroxy-isoindole-1,3-dione

생성물 1

HCID 68088839(S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-5-hydroxy-isoindole-1,3-dione

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of (S)-4-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-5-hydroxy-isoindole-1,3-dione (1 mmol) in anhydrous CH2Cl2 (20 mL), is added iodotrimethylsilane (6 mmol). The mixture is stirred at room temperature for 24 hours. This mixture is diluted with brine (20 mL) and is extracted with CH2Cl2 (2×30 mL). The extracts are combined, and the solvent is removed in vacuo to give crude (S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-5-hydroxy-isoindole-1,3-dione. The product is purified by column chromatography.

후처리

  1. extractionis extracted with CH2Cl2 (2×30 mL)
  2. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-09724ddea3de4fb1b1b793ae830a32ec
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853175B2

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