Hydroxyamine hydrochloride → tert-Butyl N-allyl-N-[2-hydroxyimino-2-phenyl-ethyl]carbamate

HRID 338090ノート

反応式

HRID 338090 の反応式
[CH2:1]([N:4]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([N:4]([CH2:12][C:13](=[N:22][OH:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86697893tert-Butyl N-allyl-N-phenacyl-carbamate

生成物 1

HCID 86697903tert-Butyl N-allyl-N-[2-hydroxyimino-2-phenyl-ethyl]carbamate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of tert-butyl N-allyl-N-phenacyl-carbamate (3.2 g, 11.6 mmol), hydroxylamine hydrochloride (1.2 g, 17.4 mmol) and sodium acetate (1.4 g, 17.4 mmol) in ethanol (46 mL) is stirred at 70° C. for 18 hours. The reaction is cooled, diluted with water and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as a mixture of E and Z isomers which is used without further purification (3.16 g, 94%). ES/MS (m/e): 191 (M+H-100).

後処理

  1. temperatureThe reaction is cooled
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-00994f3fa7044d94b2cf42d6c74d66cc
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

反応ノート

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