Sodium Iodide → 1-(Phenyloxycarbonyloxy)pentyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

HRID 36791Notes

Reaction equation

[C:1](=[O:16])([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2][CH:3](Cl)[CH2:4][CH2:5][CH2:6][CH3:7].[C:17]([NH:20][C:21]1[C:22]([I:37])=[C:23]([N:32]([C:34](=[O:36])[CH3:35])[CH3:33])[C:24]([I:31])=[C:25]([C:28]([O-:30])=[O:29])[C:26]=1[I:27])(=[O:19])[CH3:18].[K+].[I-].[Na+]>CN(C=O)C>[C:17]([NH:20][C:21]1[C:22]([I:37])=[C:23]([N:32]([C:34](=[O:36])[CH3:35])[CH3:33])[C:24]([I:31])=[C:25]([C:28]([O:30][CH:3]([O:2][C:1]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])[CH2:4][CH2:5][CH2:6][CH3:7])=[O:29])[C:26]=1[I:27])(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Chloropentyl phenyl carbonate (0.14 g, 0.58 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (0.35 g, 0.53 mmol) and sodium iodide (0,008 g, 0.053 mmol) in dry DMF (3 ml). After stirring at 50° C. for 5 hours and at room temperature for 2 days the solvent was removed at reduced pressure. The residue was suspended in chloroform (15 ml) and washed four times with a saturated sodium hydrogen carbonate solution and finally twice with water. After drying with magnesium sulfate the solution was evaporated to dryness. Yield: 0.04 g. Purity by HPLC: 94.8% 1H-NMR (DMSO-d6): delta=0.92(CH3CH2); 1.31-1.55 (CH3CH2CH2); 1.68 (NCH3COCH3); 2.04 (CH2CH); 2.05 (NHCOCH3); 2.97 (NCH3); 6.95 (CH); 7.27-7.49 (phenyl); 10.13 ppm (NH). FAB/MS: 835 ((M+H)+).

Workup

customwas removed at reduced pressure
washwashed four times with a saturated sodium hydrogen carbonate solution
dry with materialAfter drying with magnesium sulfate the solution
customwas evaporated to dryness

Sources & evidence

ORD record: ord-c317ffa6ffad4aabb1fe837f8f4d02de
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416223

Reaction notes

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