Cyclohexanecarboxylic acid → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-cyclohexylcarbonyloxyethylthio)acetamide

HRID 52055ノート

反応式

HRID 52055 の反応式
ClC(OCC)=O.[CH:7]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[N:16]1([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([O:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][NH:34][C:35](=[O:41])[CH2:36][S:37][CH2:38][CH2:39]O)[CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(OCC)(=O)C>[N:16]1([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([O:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][NH:34][C:35](=[O:41])[CH2:36][S:37][CH2:38][CH2:39][O:14][C:13]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)=[O:15])[CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 7413Cyclohexanecarboxylic acidHCID 10928Ethyl chloroformateHCID 67725880N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide

生成物 1

HCID 67725868N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-cyclohexylcarbonyloxyethylthio)acetamide収率 35%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

0.10 ml of ethyl chloroformate was added, whilst ice-cooling, to a solution of 0.13 ml of cyclohexanecarboxylic acid in 18 ml of ethyl acetate, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, a solution of 0.40 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide (prepared as described in Example 1) in 4 ml of ethyl acetate was added to the reaction mixture, whilst ice-cooling. The reaction mixture was then stirred at room temperature for 1 hour, after which it was heated under reflux for 16 hours. At the end of this time, it was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.18 g of the title compound in a 35% yield.

後処理

  1. temperaturecooling
  2. stirringThe reaction mixture was then stirred at room temperature for 1 hour
  3. temperatureafter which it was heated
  4. temperatureunder reflux for 16 hours
  5. concentrationAt the end of this time, it was concentrated by evaporation under reduced pressure
  6. customThe concentrate was purified by column chromatography through silica gel
  7. additionby volume mixture of methanol and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-abb5572c69ee4e9996c29ebd2e514ffc
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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