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Sodium Iodide → (2-Benzyloxycarbonylamino-ethyl)-phosphonic acid monoethyl ester

HRID 1886998
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1886998
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:8])[O:5]CC)[CH3:2].[Na+].[I-]>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:5])[OH:8])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 12487964(2-Benzyloxycarbonylamino-ethyl)-phosphonic acid diethyl ester

Produkt 1

HCID 71420008(2-Benzyloxycarbonylamino-ethyl)-phosphonic acid monoethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

(2-Benzyloxycarbonylamino-ethyl)-phosphonic acid diethyl ester (5.77 g, 18.3 mmol) was dissolved in pyridine (61 mL). To this solution was added NaI (13.7 g, 92 mmol). The mixture was heated at 115° C. overnight. The next day the reaction was determined, by LC/MS, to be largely complete. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in H2O and extracted with Et2O. The water was then cooled in an ice bath and the adjusted to pH 2 with 2N HCl. The water was then extracted with CH2Cl2 and the combined organic layers were washed with brine and dried over Na2SO4. The drying agent was removed by vacuum filtration and the filtrate was concentrated to yield (2-benzyloxycarbonylamino-ethyl)-phosphonic acid monoethyl ester (4.68 g, 89%) as an oil that turned to a waxy solid under high vacuum.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in H2O
  4. extractionextracted with Et2O
  5. temperatureThe water was then cooled in an ice bath
  6. extractionThe water was then extracted with CH2Cl2
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. customThe drying agent was removed by vacuum filtration
  10. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d261b7406f6c4fe09e889539eb9ef12c
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501714B2

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