Benzyl chloroformate → 1-Benzyloxycarbonylamino-2-phenylethylphosphonous acid

HRID 1376426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376426
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]([P:21]([OH:23])[OH:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[Na+].O.O1CCOCC1>[CH2:5]([O:4][C:2]([NH:12][CH:13]([P:21]([OH:23])[OH:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 2

HCID 10387Benzyl chloroformateHCID 229165291-Amino-2-phenylethylphosponous acid

Produkt 1

HCID 145513411-Benzyloxycarbonylamino-2-phenylethylphosphonous acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2.25 ml (14.25 mmol) of benzyl chloroformate are added dropwise, at 0° C. and within the space of 30 min., to a suspension of 1.76 g (9.5 mmol) of 1-amino-2-phenylethylphosponous acid in 15 ml of 1M NaOH, 5 ml of water and 5 ml of dioxane. During a further 2.5 h of stirring at 0° C., the pH of the mixture is maintained at 9-10 using 1M NaOH (approximately 10 ml). After removing the cooling medium, the mixture is stirred at RT overnight. The reaction solution is then washed several times with diethyl ether. The aqueous phase is adjusted to pH 2, at 0°-5° C., using 6M HCl and extracted several times with ethyl acetate. The combined extracts are washed with a saturated solution of NaCl, dried with Na2SO4, filtered and subjected to rotary evaporation i.V. A solid residue remains which is recrystallized from ether/petroleum ether.

Aufarbeitung

  1. customAfter removing the cooling medium
  2. stirringthe mixture is stirred at RT overnight
  3. washThe reaction solution is then washed several times with diethyl ether
  4. customis adjusted to pH 2, at 0°-5° C.
  5. extractionextracted several times with ethyl acetate
  6. washThe combined extracts are washed with a saturated solution of NaCl
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. customis recrystallized from ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-d2956f2c407c4e0ab5daa437bf3e87f1
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663139

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