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N-Methylpiperidine → N1-[1-methyl-2-(4-trifluoromethylphenoxy)ethyl]-N2-phenoxycarbonyl-L-valinamide

HRID 1900174
ノート
印刷プレビュー

反応式

HRID 1900174 の反応式
CN1CCCCC1.[O:8]([C:15]([NH:17][C@H:18]([C:22]([OH:24])=O)[CH:19]([CH3:21])[CH3:20])=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC(C)C)=O.[CH3:33][CH:34]([NH2:47])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=1>C(Cl)Cl.O>[CH3:33][CH:34]([NH:47][C:22](=[O:24])[C@H:18]([CH:19]([CH3:20])[CH3:21])[NH:17][C:15]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:16])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:44])([F:45])[F:46])=[CH:39][CH:38]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 9816135N-Phenoxycarbonyl-L-valineHCID 132097311-[4-(Trifluoromethyl)phenoxy]-2-propanamine

生成物 1

HCID 53663619N1-[1-methyl-2-(4-trifluoromethylphenoxy)ethyl]-N2-phenoxycarbonyl-L-valinamide収率 40%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

1.6 g of N-methylpiperidine was added to a solution containing 4.0 g of N-phenoxycarbonyl-L-valine dissolved in 80 ml of methylene chloride, at -20° C. After the mixture was stirred for 15 minutes at the same temperature, 2.2 g of isobutyl chloroformate was added to the mixture, and stirred for 1 hour at -20° C. 3.5 g of 1-methyl-2-(4-trifluoromethylphenoxy)ethylamine 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, and 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 was purified by column chromatography on silica gel, thus obtaining 2.8 g of the desired product in the form of a white crystal (yield: 40%).

後処理

  1. additionwas added to the mixture
  2. temperaturewarm naturally to room temperature
  3. stirringwhile being stirred
  4. stirringwas 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. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-94cc139f9f9f478a8a4ace4bf7eb4904
出典データセット
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05574064

反応ノート

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