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

HRID 1271812Notes

Reaction equation

HRID 1271812 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9abac11493ac4164ab4a1c87ab3570b7
Source dataset
uspto-grants-2007_04
Patent number
US07208140B2

Reaction notes

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