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Ethyl bromoacetate → [(4-t-Butoxycarbonylamino-butyl)-propyl-amino]-acetic acid ethyl ester

HRID 2080874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2080874
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)(Cl)Cl>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])[CH2:13][CH2:14][CH3:15])[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 86071285(4-Propylamino-butyl)-carbamic acid t-butyl ester

Produkt 1

HCID 86614915[(4-t-Butoxycarbonylamino-butyl)-propyl-amino]-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

The compound (339.0 mg) obtained in Example 84-1 was dissolved in chloroform (5.1 ml) and added with triethylamine (0.41 ml). Ethyl bromoacetate (0.20 ml) was dropped to the solution and the whole was stirred at room temperature for 2 days. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (273.9 mg) as a colorless oily substance.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9c38f85586ec4adaa4aa19c5d7b39ffb
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932281B2

Notizen zur Reaktion

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