Triethylamine → HCID 86676231、化合物

HRID 1409082ノート

反応式

HRID 1409082 の反応式
[OH:1][CH2:2][CH:3]([N:7]([CH2:15][CH:16]=[CH2:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6].C(N(CC)CC)C.[N+:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>CN(C)C1C=CN=CC=1.ClCCl.C(=O)([O-])O.[Na+]>[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:1][CH2:2][CH:3]([N:7]([C:8]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:14])[CH2:15][CH:16]=[CH2:17])[CH2:4][CH:5]=[CH2:6])=[O:33])=[CH:35][CH:36]=1)([O-:27])=[O:26]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 86676230HCID 86676230、化合物

生成物 1

HCID 86676231HCID 86676231、化合物収率 58.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a mixture of tert-butyl [1-(hydroxymethyl)but-3-en-1-yl]prop-2-en-1-ylcarbamate (15.0 g) produced above, triethylamine (19.0 g) and dichloromethane (150 mL) was added N,N-dimethylpyridin-4-amine (0.7 g). To the mixture was added dropwise a solution of 4-nitrobenzoyl chloride (14.2 g) in dichloromethane (30 mL), and the mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate, the mixture was extracted with dichloromethane, and the extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (14.1 g).

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-100abcfb1f284debabdead76141781ee
出典データセット
uspto-grants-2014_12
特許番号
US08921354B2

反応ノート

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