Sodium Iodide → 3-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 846966Notes

Reaction equation

HRID 846966 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][O:12][C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:7])=[O:6].[I-:36].[Na+]>C(C(C)=O)C>[I:36][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][O:12][C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 148350183-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

Product 1

HCID 148350213-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropaneYield 77%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3.845 (8.18 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecyloxy-2-methoxypropane III a3 in 30 ml of methyl ethyl ketone is added 2.45 g (16.36 mM) of sodium iodide and the mixture is refluxed for 3 hours with stirring. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (4:1) mixture as an eluent. The product is recrystallied from methanol to give 3.556 g (6.332 mM) of 1-hexadecyloxy-3-(3-iodopropylsulfonylamino)-2-methoxypropane II a3 in 77% yield.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customAfter the solvent is evaporated
  3. customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (4:1) mixture as an eluent

Sources & evidence

ORD record
ord-a562143f3a204929b7c892e3b929e46d
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

Loading…