Ethyl bromoacetate → Tert-butyl 3-(4-{[(2-ethoxy-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate

HRID 1266504ノート

反応式

HRID 1266504 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1.C(N(CC)CC)C.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1)[CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH3:39]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 22708175Tert-butyl 3-(4-{[(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate

生成物 1

HCID 22708222Tert-butyl 3-(4-{[(2-ethoxy-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate収率 94%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 600 mg (1.75 mmol) of tert-butyl 3-(4-{[(2-furylmethyl)amino]-methyl}phenyl)-2,2-dimethylpropionate (Example I-5), 323 mg (0.87 mmol) of tetra-n-butylammonium iodide and 265 mg (2.62 mmol) of triethylamine in 10 ml of THF is treated with 438 mg (2.62 mmol) of ethyl bromoacetate and heated at reflux overnight. After cooling, the mixture is concentrated under reduced pressure, the residue is taken up in water and ethyl acetate, the aqueous phase is extracted 2× with ethyl acetate and the combined organic phases are washed with NaCl solution and dried over sodium sulphate. The solvent is removed under reduced pressure, and chromatographic purification on silica gel (cyclohexane→cyclohexane/ethyl acetate 10:1) then gives 702 mg (94%) of tert-butyl 3-(4-{[(2-ethoxy-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-di methylpropionate.

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated under reduced pressure
  5. extractionethyl acetate, the aqueous phase is extracted 2× with ethyl acetate
  6. washthe combined organic phases are washed with NaCl solution
  7. dry with materialdried over sodium sulphate
  8. customThe solvent is removed under reduced pressure, and chromatographic purification on silica gel (cyclohexane→cyclohexane/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-9e8185ef4827456a951f8dbbdcc854e9
出典データセット
uspto-grants-2003_04
特許番号
US06548538B2

反応ノート

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