Tetrahydrofuran → 4-{[Cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}benzoic acid

HRID 2091202ノート

反応式

HRID 2091202 の反応式
[CH:1]1([CH:7]([NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:7]([NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778727Methyl 4-{[cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}benzoate

生成物 1

HCID 667777714-{[Cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}benzoic acid収率 86.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a mixture of methyl 4-{[cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}benzoate (2.66 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20.0 mL), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20.0 mL) was added at 0° C. The resulting precipitate was collected by filtration and the obtained solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (2.22 g, 86%) as a pale-brown solid.

後処理

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (40 mL)
  5. addition1N hydrochloric acid (20.0 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration
  7. dissolutionthe obtained solid was dissolved in ethyl acetate
  8. washThe solution was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washThe residue was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-e70c0634eab343a49315b6bdd71b8054
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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