Triethylamine → (+/-)-Pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxymethyl)phenyl ester

HRID 131774

反応式

HRID 131774 の反応式
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].ClC([O:11][CH2:12][CH:13]([CH3:15])C)=O.[CH2:16](N(CC)CC)[CH3:17].[CH:23]([N:26]([CH:45]([CH3:47])[CH3:46])[CH2:27][CH2:28][CH:29]([C:36]1[CH:41]=[C:40]([CH2:42][OH:43])[CH:39]=[CH:38][C:37]=1[OH:44])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:25])[CH3:24]>ClCCl>[CH:45]([N:26]([CH:23]([CH3:25])[CH3:24])[CH2:27][CH2:28][CH:29]([C:36]1[CH:41]=[C:40]([CH2:42][O:43][C:12](=[O:11])[CH2:13][CH2:15][CH:16]=[CH2:17])[CH:39]=[CH:38][C:37]=1[O:44][C:1](=[O:7])[CH2:2][CH2:3][CH:4]=[CH2:5])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:47])[CH3:46]

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 611384-Pentenoic acidHCID 62365Isobutyl chloroformateHCID 99279712-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

生成物 1

HCID 17874072(+/-)-Pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxymethyl)phenyl ester収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A cooled (4° C.) mixture of pent-4-enoic acid, isobutyl chloroformate, and triethylamine (each 5.84 mmol) in 10 ml of dichloromethane was stirred 5 hrs under an atmosphere of dry nitrogen gas. The cooling bath was then removed and both triethylamine (1.46 mmol) and 2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethylphenol (1.46 mmol) were added in one portion. After 18 hrs the mixture was diluted with dichloromethane (30 ml), washed several times with water and finally aqueous 5% sodium hydrogen carbonate solution. After drying (sodium sulphate), filtration and evaporation the oily residue was re-dissolved in a small volume of a solvent mixture consisting of ethyl acetate/heptane/triethylamine (65/30/5, vol.-%) and applied on a silica gel flash chromatography column. Elution of the column with the same solvent mixture, collection of the appropriate fractions, and evaporation of the combined fractions gave (±)-pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxymethyl)-phenyl ester as a pale yellow syrupy oil (50% yield), tlc: (4) 0.75. NMR (CDCl3): 18.95, 20.77, 27.75, 28.87, 33.58, 36.83, 42.13, 43.72, 48.71, 65.85, 70.55, 115.47, 115.99, 122.45, 126.26, 127.08, 127.96, 128.11, 28.83, 133.73, 136.38, 136.79, 137.04, 143.77, 148.46, 171.11, 172.78.

後処理

  1. temperatureA cooled
  2. customThe cooling bath was then removed
  3. washwashed several times with water and finally aqueous 5% sodium hydrogen carbonate solution
  4. customAfter drying
  5. filtration(sodium sulphate), filtration and evaporation the oily residue
  6. dissolutionwas re-dissolved in a small volume of a solvent mixture
  7. washElution of the column
  8. customwith the same solvent mixture, collection of the appropriate fractions, and evaporation of the combined fractions

出典と根拠

ORDレコード
ord-7e2db2a550744864affa141c23fdb9ff
出典データセット
uspto-grants-2008_06
特許番号
US07384980B2

関連ノート

読み込み中…