Pyridine → (2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

HRID 457910ノート

反応式

HRID 457910 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.Cl.[CH2:19]([O:22][NH2:23])[CH:20]=[CH2:21].N1C=CC=CC=1>C(O)C>[CH2:19]([O:22][N:23]=[C:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:14]([OH:16])=[O:15])[CH2:10]1)[CH:20]=[CH2:21]

参加物

5

反応物 3

HCID 1049PyridineHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acidHCID 16211718O-Prop-2-en-1-ylhydroxylamine--hydrogen chloride--water (1/1/1)

生成物 1

HCID 58714562(2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid収率 94.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution was made containing (2S)-1-(tert-butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid (5.0 g, 22 mmol) and O-allylhydroxylamine hydrochloride monohydrate (7.2 g, 65.5 mmol) in a 1:1 mixture of pyridine and ethanol (100 ml). The reaction was heated to reflux for 2.5 h before cooling and removal of solvent. The residue was dissolved in ethyl acetate and washed rapidly with 1.3N HCl (40 ml). The acidic layer was then extracted with ethyl acetate (3×20 ml) and the combined organic layers washed with brine before drying over magnesium sulfate, filtering and removal of solvent in vacuo. The desired product (5.9 g, 94%) was isolated as a pale yellow oil.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. temperaturebefore cooling
  4. customremoval of solvent
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed rapidly with 1.3N HCl (40 ml)
  7. extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
  8. washthe combined organic layers washed with brine
  9. dry with materialbefore drying over magnesium sulfate
  10. filtrationfiltering
  11. customremoval of solvent in vacuo

出典と根拠

ORDレコード
ord-67cacd03687843d0887584299ec1b0f7
出典データセット
uspto-grants-2007_03
特許番号
US07189754B2

反応ノート

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