无水亚硫酸钠 → 1-[2-(1-Adamantyl)ethyl]-3-[3-oxo-3-(4-pyridyl)propyl]-1-pentylurea

HRID 11488

反应方程式

HRID 11488 反应方程式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]12([CH2:33][CH2:34][N:35]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:36]([NH:38][CH2:39][CH2:40][CH:41]([OH:48])[C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[O:37])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl.O.C(OCC)(=O)C>[C:23]12([CH2:33][CH2:34][N:35]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:36]([NH:38][CH2:39][CH2:40][C:41](=[O:48])[C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[O:37])[CH2:30][CH:29]3[CH2:28][CH:27]([CH2:26][CH:25]([CH2:31]3)[CH2:24]1)[CH2:32]2

参与物

8

反应物 4

HCID 24437无水亚硫酸钠HCID 159087戴斯-马丁氧化剂HCID 516892碳酸氢钠HCID 219739861-[2-(1-Adamantyl)ethyl]-3-[3-hydroxy-3-(4-pyridyl)propyl]-1-pentylurea

产物 1

HCID 219741111-[2-(1-Adamantyl)ethyl]-3-[3-oxo-3-(4-pyridyl)propyl]-1-pentylurea收率 87.8%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂HCID 8857乙酸乙酯溶剂2 次

实验过程

1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (221 mg, 0.526 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-3-[3-hydroxy-3-(4-pyridyl)propyl]-1-pentylurea (100 mg, 0.234 mmol) in anhydrous dichloromethane (2 ml) under ice-cooling, the temperature was raised to room temperature, and the mixture was stirred for one hour. The reaction mixture was cooled with ice again, ethyl acetate (10 ml), a saturated aqueous sodium sulfite solution (5 ml) and a saturated aqueous sodium hydrogencarbonate solution (5 ml) were added to the reaction mixture, and the whole was stirred for 15 minutes. The reaction mixture was distributed with ethyl acetate (50 ml) and water (10 ml), and the organic layer was washed with a saturated aqueous sodium sulfite solution (5 ml), a saturated aqueous sodium hydrogencarbonate solution (5 ml) and a saturated aqueous sodium chloride solution (25 ml) successively. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 87.3 mg (87.8%) of the titled compound as colorless crystals.

后处理

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled with ice again
  3. stirringthe whole was stirred for 15 minutes
  4. washthe organic layer was washed with a saturated aqueous sodium sulfite solution (5 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

来源与证据

ORD记录
ord-e566d59fdc5441c397562ebe5a903995
来源数据集
uspto-grants-2006_08
专利号
US07098226B2

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