Methyl Thioglycolate → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(methoxycarbonylmethylthio)pentanamide

HRID 52103

反応式

HRID 52103 の反応式
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][SH:5].[N:9]1([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]Cl)[CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O1CCCC1>[N:9]1([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][S:5][CH2:4][C:3]([O:7][CH3:8])=[O:6])[CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 67725907N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-chloropentanamide

生成物 1

HCID 67725929N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(methoxycarbonylmethylthio)pentanamide収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

344 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling and in an atmosphere of nitrogen, to a solution of 0.35 ml of methyl thioglycolate in 90 ml of tetrahydrofuran, and the resulting mixute was stirred at room temperature for 30 minutes. At the end of this time, it was cooled with ice, and a solution of 2.94 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-chloropentanamide [prepared as described in step (a) above] in 30 ml of tetrahydrofuran was added dropwise to the mixture. The reaction mixture was then stirred at room temperature for 2 hours, after which the solvent was removed by distillation 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 residue 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 2.84 g (yield 89%) of the title compound as an oil.

後処理

  1. temperatureAt the end of this time, it was cooled with ice
  2. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  3. customafter which the solvent was removed by distillation 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 residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-22f86299ab3f465e992d776440572a44
出典データセット
uspto-grants-1997_04
特許番号
US05616579

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