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

HRID 532119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532119
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-09724ddea3de4fb1b1b793ae830a32ec
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853175B2

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