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

HRID 2091202노트

반응식

HRID 2091202 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e70c0634eab343a49315b6bdd71b8054
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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