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

HRID 846968

반응식

HRID 846968 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f0775e711abf4cc1bbcad463dcea1e94
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05138067

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