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

HRID 745043Notes

Reaction equation

[C:1](=[O:13])([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[O:2][CH:3](Cl)[CH3:4].[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O-:27])=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15].[K+].[I-].[Na+]>CN(C=O)C>[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O:27][CH:3]([O:2][C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:13])[CH3:4])=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Chloroethyl hexyl carbonate (0.47 g, 2.3 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (1.51 g, 2.3 mmol) and sodium iodide (0.036 g, 0.24 mmol) in dry DMF (12 ml). After stirring at 60° C. for 3 hours and at room temperature for 18 hours the solvent was removed at reduced pressure. The residue was suspended in chloroform (20 ml) and washed three 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: 0.88 g, Purity by HPLC: 95.2% 1H-NMR (DMSO-d6); delta=0.86 (CH2CH3); 1.22-1.36 (CH2CH2CH2CH3); 1.62 (OCH2CH2); 1.64 (CHCH3); 1.66 (NCH3COCH3); 2.04 (NHCOCH3); 2.95 (NCH3); 4.16 (OCH2); 6.96 (CH); 10.11 ppm (NH). FAB/MS: 801 ((M+H)+).

Workup

customwas removed at reduced pressure
washwashed three 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-dbb5192b81e447348e297f1f8a71f53b
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559266

Reaction notes

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