Acetic Acid → 2-Methoxy-1-octadecylcarbamoyloxy-3-(3-phenylselenylpropylsulfonylamino)propane

HRID 846968Notes

Reaction equation

HRID 846968 reaction equation
C1([Se:7][Se]C2C=CC=CC=2)C=CC=CC=1.[BH4-].[Na+].[C:17](O)(=O)[CH3:18].I[CH2:22][CH2:23][CH2:24][S:25]([NH:28][CH2:29][CH:30]([O:54][CH3:55])[CH2:31][O:32][C:33](=[O:53])[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])(=[O:27])=[O:26].O1[CH2:60][CH2:59][CH2:58][CH2:57]1>C(O)C>[CH3:55][O:54][CH:30]([CH2:29][NH:28][S:25]([CH2:24][CH2:23][CH:22]([SeH:7])[C:18]1[CH:17]=[CH:60][CH:59]=[CH:58][CH:57]=1)(=[O:27])=[O:26])[CH2:31][O:32][C:33](=[O:53])[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 15460Diphenyl diselenideHCID 4311764Sodium borohydrideHCID 148350213-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

Product 1

HCID 1317170002-Methoxy-1-octadecylcarbamoyloxy-3-(3-phenylselenylpropylsulfonylamino)propaneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.52 g (4.9 mM) of diphenyl diselenide in 25 ml of dry ethanol is added 370 mg (9.78 mM) of sodium borohydride with ice-cooling and the mixture is stirred for 30 minutes. To the above mixture are added 0.56 ml (9.78 mM) of acetic acid and a solution of 1.03 g (1.63 mM) of 3-(3-iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane in 10 ml of tetrahydrofuran and the mixture is stirred at room temperature for 1.5 hours. The product is extracted with ethyl acetate, and the organic layer is washed with 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (2:1) eluent to give 1.06 g (1.60 mM) of 2-methoxy-1-octadecylcarbamoyloxy-3-(3-phenylselenylpropylsulfonylamino)propane II a1' as a colorless powder in 98% yield.

Workup

  1. temperaturecooling
  2. extractionThe product is extracted with ethyl acetate
  3. washthe organic layer is washed with 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (2:1) eluent

Sources & evidence

ORD record
ord-f0775e711abf4cc1bbcad463dcea1e94
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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