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

HRID 353169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353169
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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-dimethylpropionate.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e3885fd06ba544489631aca9839cbdaa
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750236B2

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