Propane sultone → 3-[3-(5-carboxypentyl)-4,5,6-triiodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate

HRID 508296Notes

Reaction equation

HRID 508296 reaction equation
[I:1][C:2]1[C:10]([I:11])=[C:9]([I:12])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:14])[C:5]([CH3:13])=[N:6]2.[CH2:23]1[CH2:29][S:26](=[O:28])(=[O:27])[O:25][CH2:24]1>>[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:4]1([CH3:14])[C:3]2[C:7](=[CH:8][C:9]([I:12])=[C:10]([I:11])[C:2]=2[I:1])[N+:6]([CH2:24][CH2:23][CH2:29][S:26]([O-:28])(=[O:27])=[O:25])=[C:5]1[CH3:13])([OH:22])=[O:21]

Participants

3

Reactant 2

HCID 14264Propane sultoneHCID 717361666-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid

Product 1

HCID 897815713-[3-(5-carboxypentyl)-4,5,6-triiodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonateYield 42%

Procedure

600 mg (0.94 mmol) of 6-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid was heated with 600 mg (4.7 mmol) of 1,3-propane sultone at 100° C. for 40 minutes. The raw product was column purified (Silica gel 60, 0-40% methanol-chloroform) to give 300 mg of 3-[3-(5-carboxypentyl)-4,5,6-triiodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate: 7.39 (1H, s, arom.), 4.31 (2H, m, NCH2), 3.27 (3H, s, CH3), 2.34-2.02 (2H, m, CH2), 2.19 (2H, t, CH2CO), 1.98-1.65 (4H, m, CH2), 1.31 (3H, s, CH3), 1.43-1.00 (4H, m, (CH2)3), 0.62-0.35 (2H, m, CH2).

Workup

  1. custompurified (Silica gel 60, 0-40% methanol-chloroform)

Sources & evidence

ORD record
ord-7bac8a2493d04776ad7c4a9e57c542b4
Source dataset
uspto-grants-2015_08
Patent number
US09095612B2

Reaction notes

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