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Water → 2,4,6-Triiodo-1,3,5-tris-(2-tert-butoxycarbonylaminoethoxymethyl)benzene

HRID 1271812
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1271812
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]OS(C1C(C)=CC=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:22][C:23]1[C:28]([CH2:29][OH:30])=[C:27]([I:31])[C:26]([CH2:32][OH:33])=[C:25]([I:34])[C:24]=1[CH2:35][OH:36].[OH2:37]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[I:22][C:23]1[C:24]([CH2:35][O:36][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:37])=[C:25]([I:34])[C:26]([CH2:32][O:33][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:27]([I:31])[C:28]=1[CH2:29][O:30][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]
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Komponenten

7

Edukt 3

HCID 962WaterHCID 206936271,3,5-Triiodo-2,4,6-trihydroxymethylbenzeneHCID 86595648Toluenesulfonic acid-2-tert-butoxycarbonylaminoethyl ester

Produkt 1

HCID 184548882,4,6-Triiodo-1,3,5-tris-(2-tert-butoxycarbonylaminoethoxymethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433
Tetrabutylammonium hydrogen sulfate
Katalysator
HCID 1140TolueneLösungsmittel2×
HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

142 g (450 mmol) of toluenesulfonic acid-2-tert-butoxycarbonylaminoethyl ester (Canne et al., Tetrahedron Letters, 38, 1997, 3361), dissolved in 250 ml of toluene, is added in drops to a mixture that consists of 50.0 g (91.4 mmol) of 1,3,5-triiodo-2,4,6-trishydroxymethylbenzene, and 3 g (8.7 mmol) of tetrabutylammonium hydrogen sulfate in 200 ml of 32% NaOH solution and 300 ml of toluene at room temperature, and then it is stirred for 12 hours. It is mixed with water and extracted twice with 300 ml each of toluene. The combined organic phases are dried on sodium sulfate, the solvent is evaporated to the dry state and chromatographed on silica gel (mobile solvent:hexane/ethyl acetate 10:1). The fractions that contain the product are combined and concentrated by evaporation.

Aufarbeitung

  1. additionis added in drops to a mixture that
  2. extractionextracted twice with 300 ml each of toluene
  3. customThe combined organic phases are dried on sodium sulfate
  4. customthe solvent is evaporated to the dry state
  5. customchromatographed on silica gel (mobile solvent:hexane/ethyl acetate 10:1)
  6. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9abac11493ac4164ab4a1c87ab3570b7
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07208140B2

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