Ethyl Acetate → dibutyl 3-(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate

HRID 2051969ノート

反応式

HRID 2051969 の反応式
[CH2:1]([O:8][NH:9][C:10](=[O:14])[O:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].Cl[CH2:20][CH2:21][CH2:22][P:23](=[O:34])([O:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][CH2:25][CH2:26][CH2:27][CH3:28].C(OCC)(=O)C>C(O)C.C(Cl)(Cl)Cl.O>[CH2:1]([O:8][N:9]([CH2:20][CH2:21][CH2:22][P:23](=[O:34])([O:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:10]([O:11][CH2:12][CH3:13])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 255288ethyl N-phenylmethoxycarbamateHCID 2723922Sodium ethoxideHCID 20337237Dibutyl 3-chloropropylphosphonate

生成物 1

HCID 20337230dibutyl 3-(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate収率 42.8%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

A solution of ethyl N-benzyloxycarbamate (7.80 g.) in absolute ethanol (5 ml.) was added dropwise to a solution of sodium ethoxide in absolute ethanol [Na: 920 mg., absolute C2H5OH: 100 ml.] at 70° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added dropwise dibutyl 3-chloropropylphosphonate (10.8 g.), whereafter the reaction mixture was refluxed with stirring for 22 hours. The resultant mixture was cooled to give precipitates, which were filtered off. The filtrate was concentrated under reduced pressure to give a residue. To the residue was added ethyl acetate (100 ml.) and water (50 ml.). The ethyl acetate layer was separated, dried over magnesium sulfate and then concentrated under reduced pressure to give an oily residue (16.6 g.). The residue was subjected to column chromatography on silica gel with an eluent (chloroform). Fractions containing the object compound were collected and concentrated under reduced pressure to give oily dibutyl 3 -(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate (7.33 g.)

後処理

  1. temperaturewhereafter the reaction mixture was refluxed
  2. stirringwith stirring for 22 hours
  3. customto give
  4. customprecipitates
  5. filtrationwhich were filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a residue
  8. customThe ethyl acetate layer was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give an oily residue (16.6 g.)
  12. additionFractions containing the object compound
  13. customwere collected
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0e95dd514f3246018aadbc46dab0855e
出典データセット
uspto-grants-1980_01
特許番号
US04182758

反応ノート

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