Ethyl Acetate → Methyl 4-{[{2-[(4'-chloro[1,1'-biphenyl]-4-yl)methoxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

HRID 8134

反応式

HRID 8134 の反応式
Br[C:2]1[CH:37]=[CH:36][C:5]([CH2:6][O:7][C:8]2[CH:35]=[CH:34][CH:33]=[CH:32][C:9]=2[CH2:10][CH2:11][N:12]([CH2:22]OC(=O)C2C=CC=CC=2)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:54]([O:57][CH2:58]C)(=[O:56])[CH3:55]>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]3[CH:35]=[CH:34][CH:33]=[CH:32][C:9]=3[CH2:10][CH2:11][N:12]([CH2:22][C:2]3[CH:37]=[CH:36][C:55]([C:54]([O:57][CH3:58])=[O:56])=[CH:4][CH:3]=3)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:36][CH:37]=2)=[CH:41][CH:40]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86760181{[{2-[(4-Bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

生成物 1

HCID 22015030Methyl 4-{[{2-[(4'-chloro[1,1'-biphenyl]-4-yl)methoxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

300.0 mg (0.51 mmol) of methyl 4-({[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 4 are initially charged in 3 ml of dimethoxyethane and admixed successively with 101.7 mg (0.62 mmol) of 4-chlorophenylboronic acid and 0.57 ml of 2M sodium carbonate solution. 10.0 mg of dichlorobis(triphenylphosphine)palladium(II) are added, and the mixture is then heated at reflux temperature for 18 hours. The reaction solution is cooled, admixed with 20 ml of ethyl acetate and washed successively with 5% strength sodium hydrogen phosphate solution, water and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and the solvent is distilled off under reduced pressure. The crude product is chromatographed over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1.

後処理

  1. temperaturethe mixture is then heated
  2. temperatureat reflux temperature for 18 hours
  3. temperatureThe reaction solution is cooled
  4. washwashed successively with 5% strength sodium hydrogen phosphate solution, water and saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe crude product is chromatographed over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1

出典と根拠

ORDレコード
ord-5d34544f0aa64138a4ebdecdb4794fce
出典データセット
uspto-grants-2006_08
特許番号
US07087644B1

関連ノート

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