Ethylene Glycol → HCID 86646403, compound

HRID 1038277Notes

Reaction equation

HRID 1038277 reaction equation
[CH2:1]([NH:4][C:5](=[O:24])[C:6]1[C:17]([I:18])=[C:16]([N:19]=[C:20]=[O:21])[C:15]([I:22])=[C:8]([C:9]([NH:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C:7]=1[I:23])[CH:2]=[CH2:3].[CH2:25]([OH:28])[CH2:26][OH:27]>ClCCl>[CH2:12]([N:11]([CH2:14][CH:13]=[CH2:12])[C:9]([C:8]1[C:15]([I:22])=[C:16]([NH:19][C:20]([O:27][CH2:26][CH2:25][O:28][C:20](=[O:21])[NH:19][C:16]2[C:17]([I:18])=[C:6]([C:5](=[O:24])[N:4]([CH2:15][CH:8]=[CH2:9])[CH2:1][CH:2]=[CH2:3])[C:7]([I:23])=[C:8]([C:9](=[O:10])[N:11]([CH2:3][CH:2]=[CH2:1])[CH2:12][CH:13]=[CH2:14])[C:15]=2[I:22])=[O:21])[C:17]([I:18])=[C:6]([C:5](=[O:24])[N:4]([CH2:7][CH:6]=[CH2:5])[CH2:1][CH:2]=[CH2:3])[C:7]=1[I:23])=[O:10])[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 86646404HCID 86646404, compound

Product 1

HCID 86646403HCID 86646403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N′-Diallyl-2,4,6-triiodo-5-isocyanatoisophthalamide in dichloromethane was added ethylene glycol (0.5 equivalent). The reaction mixture was stirred for 18 hours and then purified by column chromatography to give (3,5-Bis-diallylcarbamoyl-2,4,6-triiodo-phenyl)-carbamic acid 2-(3,5-bis-diallylcarbamoyl-2,4,6-triiodo-phenylcarbamoyloxy)-ethyl ester. A cis-dihydroxylation using OsO4 and NMMO was performed and the crude mixture was purified by preparative HPLC to give 1,3-bis-(N,N,N′,N′-tetrakis-(2,3-dihydroxypropyl))-2,4,6-triiodo-5-ureido-isophthalamide]-2-hydroxypropane as a white powder after freeze drying.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-5df37c30a4664b17a296ecc728c5ea05
Source dataset
uspto-grants-2013_10
Patent number
US08551449B2

Reaction notes

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