Diethyl chlorophosphate → HCID 11350137, Verbindung

HRID 1091460

Reaktionsgleichung

Reaktionsgleichung von HRID 1091460
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[P:21](Cl)([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH2:24]([O:23][P:21]([NH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3)(=[O:22])[O:26][CH2:27][CH3:28])[CH3:25]

Komponenten

4

Edukt 2

HCID 13139Diethyl chlorophosphateHCID 1119635510-(Aminomethyl)[1]benzopyrano[4,3,2-de]phthalazin-3(2H)-one

Produkt 1

HCID 11350137HCID 11350137, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 49 (0.5 mmol) in anhydrous DMF (20 mL) was added diethyl chlorophosphate (1.5 mmol). After 3 hours solution was concentrated in vacuo, and 50 mL of water was added. The aqueous layer was extracted with 30 mL of EtOAc twice. Organic layers were combined and washed with 30 mL of brine. Organic layer was dried with MgSO4. Solvent was removed to afford a white solid, which was recrystallized in 10% of EtOAc in hexanes to afford a white solid 54 in 50% yield. MS (ES−): 400; Mp: 222.3-224.5° C.; 1H-NMR (CDCl3, 400 MHz): 10.21 (s, 1H), 8.10 (d, J=2.5 Hz, 1H), 8.03 (d, J=7.5 Hz, 1H), 7.79 (t, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.47 (dd, J=8.5 and 2.0 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 4.12 (m, 6H), 1.32 (t, J=6.5 Hz, 6H); Anal. Calcd. for C19H20N3O5P.(0.3H2O): C, 56.10; H, 5.10; N, 10.33. Found: C, 56.00; H, 5.03; N, 10.13.

Aufarbeitung

  1. concentrationAfter 3 hours solution was concentrated in vacuo, and 50 mL of water
  2. additionwas added
  3. extractionThe aqueous layer was extracted with 30 mL of EtOAc twice
  4. washwashed with 30 mL of brine
  5. dry with materialOrganic layer was dried with MgSO4
  6. customSolvent was removed
  7. customto afford a white solid, which
  8. customwas recrystallized in 10% of EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8e4c477adf3d49379c26682630909732
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129382B2

Verknüpfte Notizen

Wird geladen…