Sodium Carbonate → Methyl 4-(((5-ethoxy-5-oxopentyl)(2-methoxyphenethyl)amino)methyl)benzoate

HRID 2110241노트

반응식

HRID 2110241 반응식
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][N:7]([CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:5][C:4]1[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=1[O:2][CH3:1])[CH3:32]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 11231852Methyl 4-(((2-methoxyphenethyl)amino)methyl)benzoate

생성물 1

HCID 22015009Methyl 4-(((5-ethoxy-5-oxopentyl)(2-methoxyphenethyl)amino)methyl)benzoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

15.0 g (50.0 mmol) of methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate from Example I.1., 11.52 g (55.0 mmol) of ethyl 5-bromovalerate and 6.37 g (106.0 mmol) of sodium carbonate are dissolved in 30 ml of acetonitrile and heated at reflux for 18 hours. After cooling, most of the solvent is distilled off under reduced pressure and the residues are mixed with water. The mixture is extracted repeatedly with ethyl acetate, the organic phases are washed with saturated sodium chloride solution and, after drying over magnesium sulphate, the solvent is removed under reduced pressure. The crude product is purified by flash chromatography over silica gel (0.04-0.063 nm) using the mobile phase cyclohexane/ethyl acetate 4/1.

후처리

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling, most of the solvent
  4. distillationis distilled off under reduced pressure
  5. additionthe residues are mixed with water
  6. extractionThe mixture is extracted repeatedly with ethyl acetate
  7. washthe organic phases are washed with saturated sodium chloride solution
  8. dry with materialafter drying over magnesium sulphate
  9. customthe solvent is removed under reduced pressure
  10. customThe crude product is purified by flash chromatography over silica gel (0.04-0.063 nm)

출처 및 근거

ORD 기록
ord-41ad6cdba23a484e9465f0f54882b4df
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517896B2

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