Sodium Iodide → HCID 14835030, compound

HRID 728427Notes

Reaction equation

HRID 728427 reaction equation
[CH3:1][O:2][CH:3]([CH2:27][NH:28][S:29]([CH2:32][CH2:33]OS(C)(=O)=O)(=[O:31])=[O:30])[CH2:4][O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][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][CH3:25].[I-:39].[Na+]>CC(C)=O>[I:39][CH2:33][CH2:32][S:29]([NH:28][CH2:27][CH:3]([O:2][CH3:1])[CH2:4][O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][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][CH3:25])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14835029HCID 14835029, compound

Product 1

HCID 14835030HCID 14835030, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 200 mg (0.341 mM) of 2-methoxy-1-octadecylcarbamoyloxy-3-(2-methanesulfonyloxyethylsulfonylamino)propane VIa4' in 5 ml of acetone is added 200 mg (1.33 mM) of sodium iodide and the mixture is refluxed with stirring for 5 hours. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (2:1) mixture as an eluent to give 188 mg (0.296 mM) of 3-(2-iodoethylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane IIa4 in 87% yield.

Workup

  1. temperaturethe mixture is refluxed
  2. customAfter the solvent is evaporated
  3. customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (2:1) mixture as an eluent

Sources & evidence

ORD record
ord-d1311acc985f4b2f94ee9fa942c8c528
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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