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

HRID 36790Notes

Reaction equation

HRID 36790 reaction equation
[C:1](=[O:20])([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:2][CH:3](Cl)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21]([NH:24][C:25]1[C:26]([I:41])=[C:27]([N:36]([C:38](=[O:40])[CH3:39])[CH3:37])[C:28]([I:35])=[C:29]([C:32]([O-:34])=[O:33])[C:30]=1[I:31])(=[O:23])[CH3:22].[K+].[I-].[Na+]>CN(C=O)C>[C:21]([NH:24][C:25]1[C:26]([I:41])=[C:27]([N:36]([C:38](=[O:40])[CH3:39])[CH3:37])[C:28]([I:35])=[C:29]([C:32]([O:34][CH:3]([O:2][C:1]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:20])[CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:33])[C:30]=1[I:31])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 194227691-Chloro-3-phenylpropyl phenyl carbonateHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 194227531-(Phenyloxycarbonyloxy)-3-phenylpropyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-Chloro-3-phenylpropyl phenyl carbonate (0.30 g, 1.03 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methyl-amino)-2,4,6-triiodobenzenecarboxylate (0.62 g, 0.93 mmol) and sodium iodide (0.014 g, 0.093 mmol) in dry DMF (5 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: 0.26 g. Purity by HPLC: 94.4% 1H-NMR (DMSO-d6): delta=1.68 (NCH3COCH3); 2.06 (NHCOCH3); 2.38 (CH2CH); 2.83 (CH2CH2CH); 2.98 (NCH3); 7.02 (CH); 7.19-7.52 (phenyl); 10.15 ppm (NH). FAB/MS: 883 ((M+H+).

Workup

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

Sources & evidence

ORD record
ord-754c0d151ce14b429e41f0a9c9165839
Source dataset
uspto-grants-1995_05
Patent number
US05416223

Reaction notes

Loading…