Sodium Carbonate → Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

HRID 54711ノート

反応式

HRID 54711 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH:11]2[C:15]([OH:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:20]1(C)C=CC(S(O)(=O)=O)=C[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([N:8]1[C:9](=[O:18])[CH:10]2[CH:12]([CH:11]2[C:15]([O:17][CH2:20][CH3:21])=[O:16])[C:13]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 199597233-Benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

生成物 1

HCID 15713436Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate収率 726.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (1.50 g, 6.13 mmol) was suspended in ethanol (30 ml), followed by adding p-toluenesulfonic acid monohydrate (145 mg, 0.76 mmol), heating the mixture under reflux for 8 hours, adding sodium carbonate to the reaction solution for neutralization, concentrating the mixture under reduced pressure, adding a saturated aqueous sodium bicarbonate to the reaction residue, extracting it with ethyl acetate, washing the extraction solution successively with water and saturated aqueous NaCl solution, drying it over anhydrous magnesium sulfate, concentrating the resulting solution to obtain ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate (1.51 g, 5.52 mmol, 90%), and recrystallizing it from ethanol to obtain a pure product.

後処理

  1. temperatureheating the mixture
  2. temperatureunder reflux for 8 hours
  3. concentrationconcentrating the mixture under reduced pressure
  4. additionadding a saturated aqueous sodium bicarbonate to the reaction residue
  5. extractionextracting it with ethyl acetate
  6. washwashing the extraction solution successively with water and saturated aqueous NaCl solution
  7. dry with materialdrying it over anhydrous magnesium sulfate
  8. concentrationconcentrating the resulting solution

出典と根拠

ORDレコード
ord-cfda687b248c4bf8a753c8ad23c1ad55
出典データセット
uspto-grants-1997_04
特許番号
US05623078

反応ノート

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