Sodium hydride → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(acetylthio)acetamide

HRID 52109노트

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HRID 52109 반응식
[C:1]([OH:4])(=[S:3])[CH3:2].[H-].[Na+].[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][NH:25][C:26](=[O:29])[CH2:27]Cl)[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][NH:25][C:26](=[O:29])[CH2:27][S:3][C:1](=[O:4])[CH3:2])[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 67725626N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-chloroacetamideHCID 178418634HCID 178418634, 화합물

생성물 1

HCID 86750622N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(acetylthio)acetamide수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 0.47 ml of thioacetic acid in 20 ml of tetrahydrofuran was added dropwise, whilst ice-cooling and in an atmosphere of nitrogen, to a suspension of 0.29 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 20 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 2.00 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-chloroacetamide [prepared as described in step (a) above] in 20 ml of tetrahydrofuran was added dropwise to the mixture, whilst ice-cooling, after which it was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, the residue was mixed with water, and the resulting aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and ethyl acetate as the eluent, to give 1.72 g (yield 77%) of the title compound as an oil.

후처리

  1. temperaturecooling
  2. stirringafter which it was stirred at room temperature for 30 minutes
  3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  4. additionthe residue was mixed with water
  5. extractionthe resulting aqueous mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated by evaporation under reduced pressure
  7. customthe concentrate was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-c107a231c7d24ba6b3600e358636d93f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

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