Sodium Iodide → HCID 86752789, compound

HRID 964371Notes

Reaction equation

HRID 964371 reaction equation
Cl[CH:2]([O:4][C:5]([O:7][CH:8]([CH2:28][O:29][C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:9][O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:6])[CH3:3].[I-].[Na+].[C:49]([NH:52][C:53]1[C:54]([I:68])=[C:55]([C:59]([I:67])=[C:60]([NH:63][C:64](=[O:66])[CH3:65])[C:61]=1[I:62])[C:56]([O-:58])=[O:57])(=[O:51])[CH3:50].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.ClCCl>[C:64]([NH:63][C:60]1[C:59]([I:67])=[C:55]([C:54]([I:68])=[C:53]([NH:52][C:49](=[O:51])[CH3:50])[C:61]=1[I:62])[C:56]([O:58][CH:2]([O:4][C:5]([O:7][CH:8]([CH2:28][O:29][C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:9][O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:6])[CH3:3])=[O:57])(=[O:66])[CH3:65]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 2855718-Crown-6HCID 23692364Potassium 3,5-diacetylamino-2,4,6-triiodobenzoateHCID 54470746HCID 54470746, compound

Product 1

HCID 86752789HCID 86752789, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-(1-Chloroethoxycarbonyl)-1,3-dipalmitoylglycerol (1.00 g, 1.43 mmol) and sodium iodide were dissolved in a solution of potassium 3,5-diacetylamino-2,4,6-triiodobenzoate (0.88 g, 1.35 mmol) in DMF (10 ml). After 5 days stirring at 50° C. 18-Crown-6 (40 mg, 0.15 mmol) was added to the mixture which was then stirred at 50° C. for a further 3 days. The reaction mixture was diluted with dichloromethane, washed 4 times with a saturated sodium bicarbonate solution, twice with water, dried over sodium sulphate and evaporated. The residue was purified by column chromatography on silica gel using heptane-ethyl acetate (1:2) as eluent.

Workup

  1. stirringwas then stirred at 50° C. for a further 3 days
  2. washwashed 4 times with a saturated sodium bicarbonate solution
  3. dry with materialtwice with water, dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6a626e5109644ce4a610e219fe9ea15d
Source dataset
uspto-grants-1998_06
Patent number
US05767299

Reaction notes

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