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

HRID 52116노트

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HRID 52116 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-876fedf5ee654ad8b7f55b3082160c95
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

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