醋酸 → 2-Methoxy-1-octadecylcarbamoyloxy-3-(3-phenylselenylpropylsulfonylamino)propane

HRID 728426

反应方程式

HRID 728426 反应方程式
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]

参与物

7

反应物 5

HCID 176醋酸HCID 8028四氢呋喃HCID 15460二苯基二硒醚HCID 4311764硼氢化钠HCID 148350213-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

产物 1

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

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

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 IIa1' as a colorless powder in 98% yield.

后处理

  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

来源与证据

ORD记录
ord-678f8b3ef726451ebd6be9ac672c9a3f
来源数据集
uspto-grants-1991_09
专利号
US05047540

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