N-Methylpiperidine → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamide

HRID 2394322

反応式

HRID 2394322 の反応式
CN1C[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[CH2:9][CH2:10][O:11][C:12]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])=[O:13].ClC(OCC(C)C)=O.[C:30]([C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][CH:38]([NH2:40])[CH3:39])=[CH:34][CH:33]=1)#[N:31]>C(Cl)Cl.O>[C:30]([C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][CH:38]([NH:40][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:12]([O:11][C:10]2[CH:9]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:13])[CH3:39])=[CH:34][CH:33]=1)#[N:31]

参加物

7

反応物 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 189727992-(4-Cyanophenoxy)-1-methylethylamineHCID 54269051N-(2-chloroethoxycarbonyl)-L-valine

生成物 1

HCID 53713420N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamide収率 52%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

0.5 g of N-methylpiperidine was added to a solution containing 1.1 g of N-(2-chloroethoxycarbonyl)-L-valine dissolved in 40 ml of methylene chloride, at -20° C. After the mixture was stirred for 15 minutes at the same temperature, 0.7 g of isobutyl chloroformate was added to the mixture at -40° C., and subsequently the whole mixture was stirred for 1 hour at -20° C. 0.9 g of 2-(4-cyanophenoxy)-1-methylethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred. The whole mixture was stirred for 20 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue, which was an oily substance, was purified by column chromatography on silica gel, thus yielding 1.0 g of the desired product in the form of colorless grains (yield: 52%).

後処理

  1. additionwas added to the mixture at -40° C.
  2. temperaturewarm naturally to room temperature
  3. stirringwhile being stirred
  4. stirringThe whole mixture was stirred for 20 hours at room temperature
  5. washAfter the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customthe methylene chloride was removed under reduced pressure
  8. customwas purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-f7a955bc8404499698dbe943abca3d53
出典データセット
uspto-grants-1998_09
特許番号
US05811424

関連ノート

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