Sodium Iodide → 3-(4-Iodobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][CH2:10][CH:11]([O:35][CH3:36])[CH2:12][O:13][C:14](=[O:34])[NH: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][CH2:32][CH3:33])(=[O:8])=[O:7].[I-:37].[Na+]>C(C(C)=O)C>[I:37][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][CH2:10][CH:11]([O:35][CH3:36])[CH2:12][O:13][C:14](=[O:34])[NH: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][CH2:32][CH3:33])(=[O:8])=[O:7]Participants
4
Procedure
To a solution of 1.23 g (2.22 mM) of 3-(4-chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane IIIa5 in 20 ml of methyl ethyl ketone is added 0.67 g (4.44 mM) of sodium iodide and the mixture is heated 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 (1:1) mixture as an eluent. The product is recrystallized from chloroform-n-hexane to give 1.16 g (1.79 mM) of 3-(4-iodobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane IIa5 in 81% yield.
Workup
- temperaturethe mixture is heated for 3 hours
- customAfter the solvent is evaporated
- customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (1:1) mixture as an eluent
- customThe product is recrystallized from chloroform-n-hexane
Sources & evidence
- ORD record
- ord-0b8e83077d9f4c4a812e3a39282bf7a2
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05047540
Reaction notes
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