1,2-Dichloroethane → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfonyl)acetamide

HRID 52116ノート

反応式

HRID 52116 の反応式
[CH3:1][S:2]([OH:5])(=O)=[O:3].[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:34])[CH2:26]SCCOC(=O)C)[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.ClC1C=[C:38](C=CC=1)[C:39]([O:41]O)=[O:40].Cl[CH2:47]CCl>>[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:34])[CH2:26][S:2]([CH2:1][CH2:47][O:41][C:39](=[O:40])[CH3:38])(=[O:5])=[O:3])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

5

反応物 4

HCID 111,2-DichloroethaneHCID 6395Methanesulfonic AcidHCID 70297m-Chloroperbenzoic acidHCID 9802303N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide

生成物 1

HCID 67725940N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfonyl)acetamide収率 40%

反応条件

温度
-10 °C

実験手順

72 μl of methanesulfonic acid were added to a solution of 0.47 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide (prepared as described in Example 2) in 5.5 ml of 1,2-dichloroethane. The resulting mixture was cooled to -10° C. 0.51 g of 3-chloroperoxybenzoic acid (purity: was added to the reaction mixture, which was then stirred at a temperature in the range from -10° C. to -5° C. for 2 hours. At the end of this time, the reaction mixture was washed with a 10% w/v aqueous solution of sodium hydrogensulfite, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, and then the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.40 g (yield 40%) of the title compound as an oil.

後処理

  1. washAt the end of this time, the reaction mixture was washed with a 10% w/v aqueous solution of sodium hydrogensulfite, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel
  4. additionby volume mixture of ethanol and chloroform as the eluent

出典と根拠

ORDレコード
ord-876fedf5ee654ad8b7f55b3082160c95
出典データセット
uspto-grants-1997_04
特許番号
US05616579

反応ノート

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