Acetic Acid → HCID 57296559、化合物

HRID 1086799ノート

反応式

HRID 1086799 の反応式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[O:2]2.C(O)(=O)C>N1C=CC=CC=1>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[O:2]2

参加物

4

反応物 2

HCID 176Acetic Acid2 回HCID 15817097Benzyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

生成物 1

HCID 57296559HCID 57296559、化合物収率 83.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Azodicarbonamide (5.0 g) was stirred with a solution of potassium hydroxide (7.0 g) in water (12 ml) at 4°. After stirring in the ice bath for 1 h the mixture was diluted with ice/water (30 ml) and the solution was filtered. The filtrate was diluted with cool (2°) ethanol (100 ml) and the resultant solid was filtered off, washed with ethanol, methanol and ether to give potassium azodicarboxylate (6.9 g). This was then mixed with 3-aza-2-oxabicyclo[2.2.1]hept-5-ene-3-carboxylic acid, (phenylmethyl) ester (0.82 g) in dry pyridine (60 ml), and acetic acid (2.02 g) was added with stirring at room temperature. After one hour a further portion of glacial acetic acid (2.02 g) was added and the reaction mixture was stirred for 15.5 h. The mixture was evaporated to dryness under reduced pressure. Further acetic acid was then added to quench the remaining yellow colour of the diimide precursor. The residue was partitioned between 0.5M citric acid (75 ml) and ethyl acetate (75 ml) and the organic phase was separated, dried, and concentrated in vacuo. The residue was purified by FCC eluting with ethyl acetate:cyclohexane (1:2) to give the title compound (0.69 g) as an oil.

後処理

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 15.5 h
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. additionFurther acetic acid was then added
  5. customto quench the remaining yellow colour of the diimide precursor
  6. customThe residue was partitioned between 0.5M citric acid (75 ml) and ethyl acetate (75 ml)
  7. customthe organic phase was separated
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by FCC
  11. washeluting with ethyl acetate:cyclohexane (1:2)

出典と根拠

ORDレコード
ord-4c047233d4c94640b5d8d567cae3ffc3
出典データセット
uspto-grants-1991_07
特許番号
US05032583

反応ノート

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