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

HRID 52055

반응식

HRID 52055 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abb5572c69ee4e9996c29ebd2e514ffc
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

연결된 노트

불러오는 중…