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Hydrochloric Acid → (2-Benzyloxycarbonylamino-ethyl)-phosphonic acid diethyl ester

HRID 1614910
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1614910
Cl.[CH2:2]([O:4][P:5]([CH2:10][CH2:11][NH2:12])(=[O:9])[O:6][CH2:7][CH3:8])[CH3:3].[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH2:7]([O:6][P:5]([CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=[O:9])[O:4][CH2:2][CH3:3])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 2733596Diethyl (2-aminoethyl)phosphonate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The HCl salt of (2-amino-ethyl)-phosphonic acid diethyl ester (4.5 g, 20.7 mmol) was dissolved in CH2Cl2 (100 mL). To this solution was added CBzCl (3.2 mL, 22.7 mmol), followed by iPr2NEt (14.4 mL, 82.8 mmol). The reaction was stirred at room temperature until complete, as determined by TLC (eluent: 100% EtOAc). The reaction was quenched by the addition of saturated NaHCO3. The mixture was then partitioned between CH2Cl2 and H2O. The layers were separated and the organic layer was washed with brine and then dried over Na2SO4. The drying agent was removed by vacuum filtration and (2-benzyloxycarbonylamino-ethyl)-phosphonic acid diethyl ester was isolated from the concentrated filtrate by silica gel column chromatography (EtOAc/hexanes) (5.98 g, 92%).

Aufarbeitung

  1. customThe reaction was quenched by the addition of saturated NaHCO3
  2. customThe mixture was then partitioned between CH2Cl2 and H2O
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe drying agent was removed by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-b1d439d00c2d435ab18937b37453f277
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765722B2

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